Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(10-oxo-decyloxy)-tetrahydro-pyran-4-yl ester | 211233-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(10-oxo-decyloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(10-oxodecoxy)oxan-2-yl]methyl acetate
• CAS: 211233-16-8
• 化学式: C₂₄H₃₉NO₁₀
• 分子量: 501.574
• InChiKey: PFCUDTZJDNKZKO-MRKXFKPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  35
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(10-oxo-decyloxy)-tetrahydro-pyran-4-yl ester 在 sodium methylate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 生成 (Z)-Octadec-9-enoic acid (R)-2-({2-[10-((2R,3R,4R,5S,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-decylamino]-ethoxy}-hydroxy-phosphoryloxy)-1-((Z)-octadec-9-enoyloxymethyl)-ethyl 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
• 作为产物：
  描述：

  1,10-癸二醇 在 重铬酸吡啶 、 无水碳酸镉 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.5h， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(10-oxo-decyloxy)-tetrahydro-pyran-4-yl 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