• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    A process is disclosed for production of a sugar ketal, which comprises reacting a sugar with a ketone in the presence of hydrogen iodide. The formation of unfavorable by-products can be reduced to a trace amount. The process offers the objective ketal in improved yields, and an industrially advantageous process.
    公开号:SU1375142A3
    申请号:SU833567940
    申请日:1983-03-25
    公开日:1988-02-15
    发明作者:Матсумура Коиси；Аоно Тетсуа
    申请人:Такеда Кемикал Индастриз Лтд (Фирма)；
    IPC主号:
    专利说明:

    113751422
    The invention relates to organo- (i () - (ft) used in the synthesis of synthesis, namely the method of various sugars and their derivatives: the production of sugar ketals of the formulas "-" ttl
    CNG-OyRi
    5 HCf-O R,
    TO
    / about in L-YAL,
     nH (P nH (No.
    Y-f 1 vT 1
    X YХД /
    the formula (g):
    -OS / RI-oHv,
    SN
    5 HCf-
    : jCi
    ten
    CH
    - V
    -0 X
    2) X + Y
    -0./Bi
    + Y v
    / V
    or A + X ".
    .
    in H
    ,
    A or F-OS / R Z OH; B H
    -oAR,
    (i () - (ft) apply various sugars and "-" tt l
    CNG-OyRi
    HCf-O R,
    : jCi (111)
    V
    l
    .
    , X OH, in H
    in H
    -oAR,
    -Ov / RI
    3) A "X Y
    Th formula (fi):
    in + Y XZ CH, OH
    .
    +
    Y.
    -Yyki
    -o,
    OH.
    in the formula (g): -O
    PA
    X2.-HC-OV / RL
    ns-o R,
      moreover, R R, j is methyl or R 7 cyclohexylidene.
    The aim of the invention is to pro. method and expansion of the assortment of the target product.
    The goal is achieved by using hydrogen iodide as a catalyst and carrying out the process at AO-EZ C.
    Example 1. To a mixture of 100 ml. cyclohexanone and 100 ml of dichloromethane, 100 g of D-arabinose and 175 mg of hydroiodic acid are added, the mixture is heated in a reflux vessel with stirring on a water bath for 6 hours. During the reaction, the refluxing plant is dried over 20 g of molecules p SIT screens placed between the reaction vessel and the cooling jacket.
    -
    ,
    to H, CH, OH in H, CH, OH

    40
    45
    50
    55
    After completion of the reaction, 0.1 ml of pyridine is added, the mixture is diluted with 200 ml of benzene, washed with 3 ml of 5% aqueous sodium bicarbonate solution, nl of water, and dried over anhydrous magnesium sulfate. The solvent and cyclohexanone are distilled off under reduced pressure.
    The output of di-0-cyclohexylidene-D-arabinoza 20.67 g
    M.p. 73.5 - 75.5 ° C (recrystallization from petroleum ether).
    Elemental analysis.
    Calculated: C, 65.78; H 8.4A.
    CpHjj Oy
    Found: C, 65.70; H 8.50.
    Example 2. To 200 ml of acetone was added 10.0 g of D-xylose and 175 mg of hydroiodic acid, the mixture was heated in a vessel under reflux with stirring for 5 hours. After completion of the reaction, 0.1 ml of pyridine is added and acetone is distilled off under reduced pressure. The precipitate is dissolved in 200 ml.
    313
    benzene, the solution is washed with 3 ml of a 5% aqueous solution of sodium bicarbonate and 2x5 ml of water, dried over anhydrous magnesium sulphate. The benzene is distilled off under reduced pressure and the residue is further distilled under reduced pressure.
    Yield 1.2: 3,5-di-o-isopropylidene- (D-chfcfuranose 12.8 g (83.6%)
    T. Kip. 94-97 C (3 mm Hg)
    Elemental analysis:
    Calculated: C 57.57; H 7.88.
    C ,, H, .Oh
    Found: C 57.33; H 7.60.
    Example 3. To a mixture of 150 ml of cyclohexanone and 120 ml of dichloromethane were added 10.0 g of D-xylose and 175 mg of hydroiodic acid, the mixture was heated in a vessel with reverse chloraxidum NICOM while stirring at 65 ° C for 8 hours. The reaction mixture is diluted with 200 ml of benzene, washed with 3 ml of 5% sodium bicarbonate solution and 2): 5 ml of water and dried over anhydrous magnesium sulfate. The solvent and cyclohexanone are distilled off under reduced pressure.
    The yield is 1.2: 3,5-di-0-cyclohexyl-ide-t-D-cxIo phyranoscine 19.8 g (96%).
    M.p. 104.5-105.5 ° C (recrystallization from petroleum ether).
    Calculated: C, 65.78; H 8.44.
    with „n„ o ,.
    Found; C 66.14; H 8.47.
    Example 4. To 200 ml of acetone was added 10.0 g of D-ribose and 175 ml of hydroiodic acid (57%), the mixture was heated in a vessel under reflux with stirring for 6 hours. After completion of the reaction, sodium bicarbonate solution was added the acetone is distilled off under reduced pressure and the residue is dissolved in 200 ml of benzene, washed with 3 ml of 5% aqueous sodium bicarbonate solution and ml of water, dried over anhydrous magnesium sulfate. The benzene is distilled off under reduced pressure and the residue is distilled under reduced pressure.
    The yield of 2.3-0-isopropylidene-D-ribofuranose 3.84 g (30%)
    T. Kip. 108-1 (0.04 mmHg
    Calculated: C 50,52; H 7.42.
    c, n, oh,
    Found: C, 50.49; H 7.40. Example5. 10.0 g of D-glucose and 100 mg are added to 200 ml of acetone.
    about 5
    Q
    five
    0
    five
    0
    five
    hydrogen iodide, the mixture is heated in a vessel under reflux with stirring for 8 hours. After completion of the reaction, 0.1 ml of pyridine is added. The acetone is distilled off under reduced pressure and the residue is dissolved in 200 ml of benzene, washed with 3 ml of a 5% aqueous solution of sodium bicarbonate, ml of water, and dried over anhydrous magnesium sulfate. The benzene is distilled off under reduced pressure.
    Yield 1.2: 5,6-di-O-isopropylidene- / -D-glucofuranose 11.5 g (80.0%).
    M.p. 107-109 ° C after recrystallization from a mixture of chloroform - gaksan (1: 2).
    Calculated: C 55.37; H 7.75,
    Ci.H ,, 0,
    Found: C 55.74; H 7.81.
    Example 6. To a mixture of 150 ml of cyclohexanone and 120 ml of dichloromethane was added 10.0 g of D-glucose and 175 mg of hydroiodic acid (57%), the mixture was heated in a reflux vessel with stirring at 65 ° C for 8 hours. The reaction mixture was diluted with 200 ml of chloroform, washed with 3 ml of 5% aqueous sodium bicarbonate solution, ml of water and dried over anhydrous. 1M magnesium sulfate. The solvent and cyclohexanone are distilled off under reduced pressure and the residue is recrystallized from ligroin.
    The yield of e 6-di-O-cyclohexnl-id- / -D-glucofuranose is 11.2 g (77.8%).
    T. pl. PZ-Pb S.
    Calculated: C 63.51; H 8.29.
    CnHjeO
    Found: C, 63.27; H 8.34.
    Example 7 To 200 ml of acetone was added. 10.0 g of D-galactose and 175 g of hydriodic acid (57%), the mixture is heated in a refluxed vessel with stirring for 8 hours. After completion of the reaction, 0.1 ml of pyridine is added, Acetone is distilled off under reduced pressure and the residue is dissolved in 200 ml of benzene, 3 ml of 5% aqueous sodium bicarbonate solution, 2 x 5 ml of water are added, dried over anhydrous magnesium sulfate. The benzene is distilled off and the residue is distilled under reduced pressure.
    Output 1.2: 3,4-di-O-isopropylidene-o-D-galactopyranose 8.5 g (59%).
    T, kip. 129-133 ° C (0.2 mm Hg)
    Calculated: C 55.37; H 7.75.
    with „n, .o,
    Found: C 55.01; H 7.80. Example 8. To 200 ml of acetone
    10.0 g of D-mannose and 100 mg of hydrogen iodide are added, the mixture is heated to reflux with stirring in a water bath at 60 ° for 5 hours. After completion of the reaction, 0.1 ml of pyridine is added. The acetone is distilled off under reduced pressure and the residue is dissolved in 200 ml of benzene, washed with 3 ml of 5% aqueous sodium bicarbonate solution, ml of water, and dried over anhydrous magnesium sulfate. The benzene is distilled off under reduced pressure.
    Vcod 2,3: 5,6-di-O-isopropshtiden- / -D-mannofuranose 11.5 g (80%).
    After recrystallization from petroyl ether, mp. 122-123 ° C.
    Calculated: C 55.37; H 7.75.
    C.jH.O,
    Found: C 55.41; H 7.78.
    Example 9. To a mixture of 150 ml. cyclohexanone and 120 ml of dichloromethane were added 10.0 g of D-mannose and 175 mg of hydroiodic acid (57%), the mixture was heated in a reflux vessel with stirring under stirring for 8 hours. The reaction mixture was diluted with 200 ml of benzene, washed with 3 ml A 5% aqueous solution of sodium bicarbonate, ml of water and dried over anhydrous magnesium sulphate. The solvent and cyclohexanone are distilled off under reduced pressure.
    Output 2,3: 5,6-di-0-cyclohexyl-ideno-y-D-mannofuranose 11.9 g (82.6% After recrystallization from cyclohexane, mp, 122-G2 4 C.
    Calculated: C 63.51; H 8.29.
    With jgH
    Found: C, 63.17; H 8.32.
    EXAMPLE 10 10 g of D-fructose and 175 mg of hydroiodic acid (57%) are added to 200 ml of acetone and the mixture is heated in a vessel under reflux with stirring for 6 hours. During this reaction, the refluxing solvent is dried with 20 g molecular sieves FOR, inserted between the reaction vessel and the cooling jacket. After completion of the reaction, 0.1 ml of pyridine is added. The acetone is distilled off under reduced pressure and the residue is dissolved in 200 ml of benzene. Benzene Solution Pro
    26
    Squeeze 3 ml of a 5% aqueous solution of sodium bicarbonate and 2x5 ml of water and dry over anhydrous magnesium sulphate. The benzene is distilled off under reduced pressure to obtain 10.7 g (74.3%) of 2,3: 4,5-di-O-isopropylidene-o-D-frucopyranose. After recrystallization from n-hexane so pl. 96-98 C. Calculated: C 55.37; H 7.75.
    about
    0
    five
    0
    Q


    five
    with "n ,, oh,
    Found: C 55.61; H 7.77.
    Example 1 1. To 200 ml of acetone was added 10.0 g of L-sorbose and 223 mg of hydroiodic acid, the mixture was heated in a vessel under reflux with stirring for 6 hours. After completion of the reaction, 0.1 ml of pyridine was added. The acetone is distilled off under reduced pressure and the residue is dissolved in 200 ml of benzene. The benzene solution is washed with 3 ml of 5% aqueous sodium bicarbonate solution, ml of water,. suiat over anhydrous magnesium sulphate. The benzene is distilled off under reduced pressure.
    The yield of 2.3: 4,6-di-0-isopropylidene-L-sorbofuranose 12.13 g (84.0%).
    M.p. 77-78 ° C (recrystallization from petroleum ether).
    Calculated: C 55.37; H 7.75.
    s, n
    Found: M 55.40; H 7.80.
    Example 12. To 200 ml of acetone was added 10.0 g of L-sorbose and 127 mg of iodine, the mixture was heated in a vessel with ob-. Refrigerate with stirring at for 6h. The reaction mixture is then subjected to subsequent processing as described in example 10.
    The yield of 2.3: 4,6-di-O-isopropylidene-L-sorbofuranose 11.15 g (77.2%), purity, 98.5%.
    Example 13. To 200 ml of acetone was added 10.0 g of L-sorbose and 81.5 mg of iodine monochloride, the mixture was heated in a reflux vessel with stirring at 60 ° C for 6 hours. The reaction mixture is then subjected to subsequent processing described in example 10.
    The yield of 2.3: 4,6-di-0-isopropylidene-L-sorbofuranose 10.9 g (75.8%), purity 97% o
    Example 14. To 200 ml of acetone were added 10.0 g of L-sorbose and 234 mg of iodine trichloride, the mixture was heated in a vessel under reflux at
    71
    stirring under stirring for 4 h. The reaction mixture is then subjected to the post-treatment described in Example 10.
    The yield of 2.3; 4,6-di-0-isopropylidene-L-sorbofuranose 9.85 g (68.2%), purity 98%.
    Example 15. 10.9 g of L-sorbose and 225 mg of N-iodosuccinimide are added to 200 ml of acetone, the mixture is heated in a vessel under reflux with stirring for 6 hours. The reaction mixture is then subjected to subsequent processing described in example 10.
    The yield of 2.3: 4,6-di-O-isopropylidene-L-sorbofuranose 8.43 g (58.4%), purity 97%.
    Example 16. To 200 ml of acetone was added 10.0 g of L-sorbose, 166 mg of potassium iodine and 152 mg of concentrated sulfuric acid, the mixture was heated in a reflux vessel while being transferred at 60 ° C for 4 h. The reaction mixture was then subjected to the processing described in example 10.
    The yield of 2.3: 4,6-di-o-isoprostadide- L-sorbofuranose 6.79 g (47.0%), purity 96%.
    Example 17. To a mixture of 150 ml of cyclohexanone and 120 ml of dichloromethane were added 10.0 g of L-sorbose and 175 mg of hydroiodic acid (57%), the mixture was heated in a refluxed vessel at 65 ° C for 8 hours. The reaction mixture is diluted with 200 ml of benzene, washed with 3 ml of a 5% aqueous solution of sodium bicarbonate, 2x5 ml of water, and dried over anhydrous magnesium sulfate. The solvent and vaclohexanone are distilled off under reduced pressure.
    The yield of 2,3: 4,6-di-0-cyclohexyl-ide-L-copbophenose 8.4 g (44.4%). After recrystallization from petroleum ether so pl. 118-119 ° C.
    Calculated: C 63.51; H 9.29.
    C,
    Found: C 63.72; H 8.24.
    Example 18. To a mixture of 150 ml of cyclohexanone and 120 ml of dichloromethane was added 10.0 g of L-sorbose and 254 mg of iodine, the mixture was heated in a reflux vessel with stirring at 65 ° C for 8 h. The reaction mixture was diluted with 200 ml benzene, washed with 3 ml of 5% water
    j
    0 5
    -


    five
    0
    five
    428
    sodium bicarbonate solution, 2x5 ml of water and dried over anhydrous magnesium sulphate. The solvent and cyclohexanone are distilled off under reduced pressure.
    The yield of 2,3: 4,6-di-0-cyclohexyl-, ide-L-copbophenose 12.3 g (65%). After recrystallization from petroleum ether. Mp. 118-119 C.
    Calculated: C 63.51; H 8.29.
     gO
    Found: C, 63.76; H 8.38.
    Example 19. To 200 ml of acetone, 10.0 g of D-mannitol and 175 ml of hydroiodic acid (57%) are added, the mixture is heated in a reflux vessel while peremestirovaniya in a water bath for 5 hours. After completion of the reaction, 0.1 ml of pyridine is added. The acetone is distilled off under reduced pressure and the residue is dissolved in 200 ml of chloroform. The solution was washed with 3 ml of a 5% aqueous solution of sodium bicarbonate and water, and dried over anhydrous magnesium sulphate. Chloroform was distilled off under reduced pressure.
    Yield 1.2: 3.4: 5,6-tri-O-isopropylidene-D-mannitol 15, O g (90%). After recrystallization from 70% nola m.p. 68.5-70.5 C.
    Calculated: C 59,58; H 8.67.
    75-
    Found: C, 59.77; H 8.58.
    Example 20 To 200 ml of acetone was added 10.0 g of L-sorbose and 57 mg of two-phosphorus tetraiodide, the mixture was heated in a vessel under reflux with stirring at 60 ° C for 4 hours. tzrimer 10.
    The yield of 2.3: 4,6-di-0-isopropylidene-L-sorbofuranose 8.60 g (59.5%), purity}, 90%.
    Example 21: To 200 ml of acetone, 10.0 g of L-sorbose, 90 mg of hydroiodic acid (57%) and 50.8 mg of iodine are added, the mixture is heated in a reflux vessel with stirring, with stirring for 8 hours. The reaction mixture is then subjected to the subsequent processing described in example 10.
    The output of 2.3: 4,6-di-0-isopropylidene-L-sorbofuranose 12,07 g (83,6%), purity 98% ..
    Example 22, To 200 ml of acetone was added 10.0 g of L-sorbose, 127 mg of iodine and 110 mg of an aqueous solution of phosphoric, fornavigate acid (about 30%), the mixture is heated in a reflux vessel with stirring with over 6 h. The reaction mixture is then subjected to subsequent processing described in example 10. JQ
    Output 2,3: A, 6-di-O-isopropylidene-L-sorbofuranose 11.56 g (80%), 98% purity.
    Example 23. 600 ml of cyclohexane, 30.0 g of D-fructose and 270 mg of 15 iodine are placed in a round bottom flask equipped with an addition funnel and a reflux condenser. The mixture is heated in an oil bath at 85-95 ° C for 9 hours. The reaction is carried out with stirring 20 under reduced pressure of 55-60 mm, Hg. Art. and continuously pouring cyclohexane into the flask (water content 150 ppm) at a rate of about 300 ml / h. 25
    On the other hand, a cyclohexane race (boiling temperature at this pressure of 78-82 ° C) at a rate of about 300 ml / h is carried out in order to keep the amount of cyclo-JQ hexane in the system where the reaction takes place at a constant level. .
    After completion of the reaction, 3 ml of an aqueous solution of sodium hydroxide (20%) are added to the mixture, the solvent is distilled off and cyclohexane is removed under reduced pressure. The residue is extracted with 1 l of benzene and the resulting solution is washed with water and dried over. anhydrous sodium sulfate. After distillation of the solvent under reduced. . pressurized, filter the product, wash it with n-hexane, containing a small amount of ether, and dry. The yield of 2,3: 4,5-di-0-cyclohexyl-idene - /) - B-fructopyranose 46.1 g (81.3%). After recrystallization from p-qi: logexane, mp, 142.5-145 ° C. IR spectra (prism KBG),; 3450; NM (df - DMSO): 1.1-1.8 (broad peak, 20H); 3.2-4.3 (t, 7H); 5.05 (d, 1H).
    Calculated: C 63.51; H 8.29.
      . ; Received; C 63.89; H 8.40. "
    PRI me R 24, 1 l of acetone,. 50.0 g of sorbose and 1.45 g of iodide acid (57%) are placed in a flask
    35
    45
    50
    Q
    5 0 5
    Q


    five
    five
    0
    equipped with a dropping funnel and a dephlegmator. The mixture is heated in a vr - bath at 42 - for 10 h. The reaction is carried out with stirring under reduced pressure (400 mm Hg), and dried acetone (water content 4il50 ppm) is continuously poured into the flask at a rate of about 500 ml / min.
    On the other hand, acetone is distilled off (a boil at this pressure of 40-42 C) at a rate of about 500 ml / h in order to ensure a constant amount of acetone in the system where the reaction takes place.
    After completion of the reaction, 5 ml of an aqueous solution of sodium hydroxide was added to the mixture, and acetone was distilled off under reduced pressure. The residue was extracted with 800 ml of benzene, the resulting solution was washed with an aqueous solution of sodium bicarbonate, water, and dried over anhydrous sodium sulfate. The benzene is distilled off under reduced pressure. The yield of 2.3: 4,6-di-O-isopropylidene-1) -orbofuranose is 63.9 g (88.5%).
    -Pr-meter. 25. To a mixed solution consisting of 100 ml of cyclohexanone and 100 ml of dichloromethane was added 10.0 g of D-fructose and 76.2 mg of iodine and the resulting mixture was heated under reflux with stirring. on a water bath having a temperature of 68 ° C for 7 hours. In the course of the reaction, the refluxed solvent is dried on 20 g of MHA screens placed between the reaction vessel and the condenser. After completion of the reaction, a small amount of pyridine is added to the reaction mixture and the solvent is distilled off under reduced pressure. The residue is dissolved in 200 ml of benzene and the benzene solution is washed with water, dried (Na,) and the solvent is frozen under reduced pressure until solidified. The solid is isolated by filtration, washed with n-hexane containing a small amount of ether, and dried to form 13.75 g (72.8%) of 2.3: 4.5-di-O-cyclohexylidene-p-D-fructopyranose.
    M.p. 142.5-145 ° C (recrystallization from n-hexane).
    Calculated,%: C 63.51; H 8.29.
    C i & b 6
    Found,%: C 63.70; H 8.33.
    Example 26. To 200 ml of acetone was added 10.0 g of L-rhamnose and 203.2 m of iodine, the mixture was heated under reflux with stirring on a water bath having a temperature of 60 ° C for 8 hours. During the reaction, a refluxed solvent dried on 20 g of molecular SIT screens placed between the reaction vessel and the cooling jacket. After completion of the reaction, a small amount of pyridine is added. Then acetone is distilled off under reduced pressure and the residue is dissolved in benzene. The resulting solution is washed with water and
    / Ov b / -4 1,
    CHN liX (I) nX ("
    N-f ZV-f Zi
    i YXi YI
    X y
    in formula i
    1) Z + Y
    -OyE, -l,
    or
    2) X + Y
    -Yybi
    -A,
    Z - OH
    -0h / r
    3) A + X in h + Y Z - -CH.OH
    , -oAp
    in the formula §
    Z..Y ,,
    in the formula
    X2-HC-Ov.Rl
    NS-0
    R
    moreover, R, i is methyl or R + R 7 is cyclohexylidene, by reacting 55 sugars, deoxy sugars or sugar alcohol with 5 or 6 carbon atoms with a ketone of formula (V)
    five
    dried over. The benzene is distilled off and the residue is isolated and purified by chromatography on silica gel with the formation of 7.85 g (63.1%) of 2.3-0-isopropylidene-a-b-Ramnoda. After recrystallization from petroleum ether, the product melts at 87 -88 ° C
    Calculated: C 52.93; H 7.90,
    C, H ,, 0,
    Found: C, 52.95; H 7.88,
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining sugar ketals formulas
    0
    CHr
    I
    r
    -OS / RI,
    one
    (Ih)
    OH, in - H
    H
    ,
    in - H
    X-0h / RI
    V .K - H, B, - H
    HI
    50
    -
    RC
    where R and R have the indicated values in the presence of a catalyst for 4-10 hours, characterized in that, in order to simplify the process and expand the range of the target product, hydrogen iodide is used as a catalyst and the process is carried out at 40-95 ° C
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    同族专利:
    公开号 | 公开日
    JPS58167582A|1983-10-03|
    DK140183A|1983-09-30|
    US4464530A|1984-08-07|
    DK155010C|1989-06-12|
    JPH0366314B2|1991-10-16|
    DE3360958D1|1985-11-14|
    DK140183D0|1983-03-28|
    HU189256B|1986-06-30|
    DK155010B|1989-01-23|
    ZA832077B|1983-12-28|
    EP0091223B1|1985-10-09|
    KR840004124A|1984-10-06|
    EP0091223A1|1983-10-12|
    KR880001867B1|1988-09-23|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3607862A|1969-02-04|1971-09-21|Hoffmann La Roche|Process for preparing carbohydrate ketals|
    US3598804A|1969-02-04|1971-08-10|Hoffmann La Roche|Preparation of ketals|
    GB1286143A|1969-02-04|1972-08-23|Roche Products Ltd|The manufacture of ketal sugars|JPS6069092A|1983-09-27|1985-04-19|Takeda Chem Ind Ltd|Production of sugar ketal|
    JPS6072895A|1983-09-28|1985-04-24|Takeda Chem Ind Ltd|Production of ketal of 2-ketogulonic acid and its ester|
    JPH0629198B2|1984-10-19|1994-04-20|武田薬品工業株式会社|Chemical dehydration method|
    DE3505150A1|1985-02-15|1986-08-21|Basf Ag, 6700 Ludwigshafen|METHOD FOR PRODUCING SUGAR KETALES|
    USH708H|1986-04-17|1989-11-07|Method of producing diacetone sorbose|
    US4965354A|1988-02-26|1990-10-23|Taito Company, Ltd.|Process for producing a condensed polysaccharide|
    DE4303821A1|1993-02-10|1994-08-11|Boehringer Ingelheim Kg|Process for the preparation of 1,2-5,6-diacetone-D-glucose|
    WO2008131024A1|2007-04-17|2008-10-30|Board Of Regents, The University Of Texas System|Iodo-hexose compounds useful to treat cancer|
    ES2628180T3|2008-07-11|2017-08-02|Board Of Regents, The University Of Texas System|New 2-deoxy monosaccharide acetates with anticancer activity|
    JP6545660B2|2013-04-05|2019-07-17|ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム|Esters of 2-deoxy-monosaccharides with antiproliferative activity|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP57050574A|JPH0366314B2|1982-03-29|1982-03-29|
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