2,3,4,6-O-四苄基-α-D-葡萄糖 | 38768-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,3,4,6-O-四苄基-α-D-葡萄糖
• 英文名称: 2,3,4,6-Tetra-O-benzyl-α-D-glucose
• 英文别名: 2,3,4,6-tetra-O-benzyl-D-glucopyranose；2,3,4,6-Tetra-O-benzyl-D-glucose；2,3,4,6-tetra-O-benzylglucose；2,3,4,6-Tetra O-benzyl D-glucose；2,3,4,6-Tetra-O-benzyl D-glucose；(2R,3S,4R,5R)-5-hydroxy-2,3,4,6-tetrakis(phenylmethoxy)hexanal
• CAS: 38768-81-9
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: OUHUDRYCYOSXDI-KMKAFXEASA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  689.6±55.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-O-四苄基-α-D-葡萄糖 在 氨 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以74%的产率得到2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl amine
  参考文献：
  名称：

  Aebischer, Bernard M.; Hanssen, Harald W.; Vasella, Andrea T., Journal of the Chemical Society. Perkin transactions I, 1982, # 9, p. 2139 - 2148

  摘要：

  DOI：

文献信息

• Derivatives of hydrazino-monosaccharides and aldohexoses which are
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：US04021542A1

  公开（公告）日：1977-05-03

  Substituted hydrazino- and pyrazolo-aldopentoses and aldohexoses, which are useful as intermediates for preparing compounds, as compounds which lower the uric acid level in the blood, and as bactericides, are provided. The substituted hydrazino compounds also enter into chemical reactions which are not possible with their unsubstituted counterparts.

  提供了替代的肼基和吡唑基醛基五糖和六糖，它们可作为制备化合物的中间体，降低血液中尿酸水平的化合物，以及杀菌剂。这些替代的肼基化合物还参与了无法与其未取代的对应物发生的化学反应。
• C-nucleoside studies. Part 13. A new synthesis of 2,3,5-tri-O-benzyl-α(and β)-<scp>D</scp>-ribofuranosylethyne involving benzyloxy participation, and a synthesis of α-showdomycin
  作者：Gaffar Aslani-Shotorbani、J. Grant Buchanan、Alan R. Edgar、Colin T. Shanks、Gavin C. Williams

  DOI：10.1039/p19810002267

  日期：——

  when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0–5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-α(and β)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-α-D-ribofuranosylmaleimide, the α-isomer of showdomycin, from (20) is described.

  2,3,4,6-四- ö苄基d -glucitol（5）反应以甲苯p -磺酰基氯在吡啶中于60℃，以形成主要是呋喃产物2,3,6-三ö -苄基-1,4-脱水-D-葡萄糖醇（10）及其5-甲苯-对磺酸酯（11），但失去4- O-苄基。该吡喃产物四ö苄基1,5-脱水- d -glucitol preponderates当中间2,3,4,6-四ö -toluene- p -sulphonyl- d -glucitol（6）转化成其0–5氧阴离子。在新合成的2,3,5-tri- O中已经利用了苄氧基的参与苄基α（及β） - d -ribofuranosylethyne，（20）和（4），从2,3,4,5-四ö苄基醛基- d -核糖。描述了由（20）合成2-α- D-呋喃呋喃糖基马来酰亚胺（Showdomycin的α-异构体）。
• C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide
  申请人：Ohio State Research Foundation

  公开号：US05516792A1

  公开（公告）日：1996-05-14

  The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide and N-glycoside analogue of retinoyl .beta.-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; 4-(retinamido)phenyl-C-xyloside, 1-(B-D-glucopyranosyl) retinamide and 1-(D-glucopyranosyluronosly) retinamide. The invention also relates to a method for making such drugs.

  本发明提供了乳腺癌化学预防芳胺类类似物，更具体地说是N-(4-羟基苯基)视黄酸-O-葡萄糖醛酸酯的C-糖苷类似物和视黄酰β-葡萄糖醛酸酯的N-糖苷类似物，这些类似物既能抵抗β-葡萄糖苷酶介导的酶解，也能抵抗酸催化的水解。具体来说，这些药物包括4-(视黄酰胺基)苯基-C-葡萄糖醛酸酯；4-(视黄酰胺基)苯基-C-葡萄糖苷；4-(视黄酰胺基)苯基-C-木糖苷；4-(视黄酰胺基)苯基-C-葡萄糖苷；4-(视黄酰胺基)苯基-C-葡萄糖醛酸酯；4-(视黄酰胺基)苯基-C-木糖苷；1-(B-D-葡萄糖吡喃基)视黄酰胺和1-(D-葡萄糖吡喃醛基)视黄酰胺。本发明还涉及制备这些药物的方法。
• Glycosylated Warfarin Analogs and Uses Thereof
  申请人：Thorson Jon S.

  公开号：US20100267655A1

  公开（公告）日：2010-10-21

  The present invention discloses a set of glycosylated warfarin analogs which are useful as anti-tumor or anti-metastatic agents and as reagents for studying sugar uptake in cells.

  本发明公开了一组糖基化华法林类似物，可用作抗肿瘤或抗转移剂，并作为研究细胞糖吸收的试剂。
• Smoking compositions containing a menthol-release additive
  申请人：Philip Morris Incorporated

  公开号：US05139034A1

  公开（公告）日：1992-08-18

  In one embodiment, this invention provides a smoking composition which contains a flavorant additive which releases menthol under normal cigarette smoking conditions. The menthol-release additive is a mixture of menthyloxycarbonylglucose compounds which include more than 35 mole percent of 1-O-menthyloxycarbonyl-.beta.-D-glucopyranose and more than about 20 mole percent of 1,6-di-O-menthyloxycarbonyl-.beta.-D-glucopyranose.

  在一个实施例中，这项发明提供了一种含有香味添加剂的吸烟组合物，该添加剂在正常吸烟条件下释放薄荷脑。薄荷释放添加剂是一种含有超过35摩尔百分比的1-O-薄荷氧羰基-β-D-葡萄糖吡喃糖和超过约20摩尔百分比的1,6-二-O-薄荷氧羰基-β-D-葡萄糖吡喃糖的化合物混合物。