(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(10-oxo-decyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 211233-15-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(10-oxo-decyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 211233-15-7
• 化学式: C₂₃H₃₆O₁₁
• 分子量: 488.532
• InChiKey: BZYKZBZISZDCIC-YKZCJQPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  34.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(10-oxo-decyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium methylate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  The synthesis of neoglycophospholipid conjugates via reductive amination of ω-oxoalkylglycosides and phosphatidylethanolamines

  摘要：

  Phospholipid conjugates of mono- and disaccharides tethered with an n-decanyl spacer were efficiently synthesized via an improved reductive amination of deprotected omega-oxodecanyl beta-glycosides and phosphatidylethanolamines with or without alkenyl groups. The omega-oxodecanyl beta-glycosides were prepared by stereoselective glycosidation of glycosyl halides with l,10-decanediol followed by pyridinium dichromate oxidation. The acetyl groups of the omega-oxodecanyl beta-glycosides were removed with sodium methoxide prior to their conjugation with phosphatidylethanolamines. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00032-9
• 作为产物：
  描述：

  在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(10-oxo-decyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The synthesis of neoglycophospholipid conjugates via reductive amination of ω-oxoalkylglycosides and phosphatidylethanolamines

  摘要：

  Phospholipid conjugates of mono- and disaccharides tethered with an n-decanyl spacer were efficiently synthesized via an improved reductive amination of deprotected omega-oxodecanyl beta-glycosides and phosphatidylethanolamines with or without alkenyl groups. The omega-oxodecanyl beta-glycosides were prepared by stereoselective glycosidation of glycosyl halides with l,10-decanediol followed by pyridinium dichromate oxidation. The acetyl groups of the omega-oxodecanyl beta-glycosides were removed with sodium methoxide prior to their conjugation with phosphatidylethanolamines. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00032-9