(2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-((1,3-bis(benzyloxy)propan-2-yl)oxy)tetrahydro-2H-pyran | 213265-19-1

• 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: (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-((1,3-bis(benzyloxy)propan-2-yl)oxy)tetrahydro-2H-pyran
• 英文别名: (2S,3R,4S,5R,6R)-2-[1,3-bis(phenylmethoxy)propan-2-yloxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 213265-19-1
• 化学式: C₅₁H₅₄O₈
• 分子量: 794.985
• InChiKey: JMTAHERREFESHW-PKVCVKGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  59.0
• 可旋转键数：
  23.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-((1,3-bis(benzyloxy)propan-2-yl)oxy)tetrahydro-2H-pyran 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 8.0h， 以91%的产率得到甘油葡糖苷
  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：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.83h， 生成 (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-((1,3-bis(benzyloxy)propan-2-yl)oxy)tetrahydro-2H-pyran
  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