1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol | 157024-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[1,3-bis(phenylmethoxy)propan-2-yloxy]oxan-2-yl]methyl acetate
• CAS: 157024-66-3
• 化学式: C₃₁H₃₈O₁₂
• 分子量: 602.636
• InChiKey: ARWUCJZZOQBIFO-PXPWAULYSA-N

物化性质

• 沸点：
  648.3±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  43
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 1,3-二羟基-2-丙基吡喃己糖苷
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465
• 作为产物：
  描述：

  1,3-双(苄氧基)-2-丙醇 、 β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以61%的产率得到1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• Nouvelles utilisations de derivés du glycerol, notamment dans le domaine cosmétique
  申请人：AGRO INDUSTRIE RECHERCHES ET DEVELOPPEMENTS (A.R.D.)

  公开号：EP1733731A1

  公开（公告）日：2006-12-20

  La présente invention concerne l'utilisation d'au moins un composé répondant à la formule (I) suivante : dans laquelle R1 représente H ou un groupe acyle, R2 représente notamment H ou un groupe acyle, et R3 représente H ou un groupe de formule suivante (C) : dans laquelle R6 représente notamment un atome d'hydrogène ou un groupe acyle, et R7 représente notamment un atome d'hydrogène ou un groupe acyle, pour la préparation d'une composition cosmétique, d'une composition pharmaceutique destinée au traitement des cancers n'impliquant pas le virus EBV, notamment destinée au traitement des mélanomes, ou destinée au traitement des processus inflammatoires de la sphère buccale, ou d'une composition nutraceutique,

  本发明涉及至少一种与下式（I）相对应的化合物的用途： 其中 R1 代表 H 或酰基，R2 尤其代表 H 或酰基，R3 代表 H 或下式（C）的基团： 其中 R6 特别代表氢原子或酰基，R7 特别代表氢原子或酰基、 用于制备化妆品组合物、用于治疗不涉及 EBV 病毒的癌症（尤其是用于治疗黑 色素瘤）或用于治疗口腔炎症过程的药物组合物或营养保健组合物、
• A Simple Synthesis of Glucosyl Glycerols
  作者：Franca Marinone Albini、Carla Murelli、Giovanni Patritti、Marco Rovati

  DOI：10.1080/00397919408010167

  日期：1994.6

  Beta-D-glucopyranosides, linked to C-2 or C-3 of the glycerol aglicone moiety, were unambiguously synthesized.
• Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol
  作者：Diego Colombo、Federica Compostella、Fiamma Ronchetti、Antonio Scala、Lucio Toma、Harukuni Tokuda、Hoyoku Nishino

  DOI：10.1016/s0968-0896(99)00137-6

  日期：1999.9

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.
• Synthesis of Glycosyl Glycerols and Related Glycolipids
  作者：René Suhr、Oliver Scheel、Joachim Thiem

  DOI：10.1080/07328309808007465

  日期：1998.8.1

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.