(2R,3R,4S)-Methyl 3-acetamido-2-acetoxy-4-methylpalmitate | 138754-67-3

• 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: (2R,3R,4S)-Methyl 3-acetamido-2-acetoxy-4-methylpalmitate
• 英文别名: methyl 3-acetamido-2-acetoxy-4-methylpalmitate；methyl (2R,3R,4S)-3-acetamido-2-acetyloxy-4-methylhexadecanoate
• CAS: 138754-67-3
• 化学式: C₂₂H₄₁NO₅
• 分子量: 399.571
• InChiKey: AWLNAZUCAPYOEX-IOMROCGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,3S,4S)-2,3-Epoxy-4-methyl-1-hexadecanol 在 palladium on activated charcoal 吡啶 、 ruthenium(II) chloride 、 sodium periodate 、 叠氮基三甲基硅烷 、 氢气 、 碳酸氢钠 、 zinc(II) chloride 作用下， 以 甲醇 、 四氯化碳 、 乙醚 、 水 、 乙腈 为溶剂， 反应 159.33h， 生成 (2R,3R,4S)-Methyl 3-acetamido-2-acetoxy-4-methylpalmitate
  参考文献：
  名称：

  Calophycin, a fungicidal cyclic decapeptide from the terrestrial blue-green alga Calothrix fusca

  摘要：

  A broad-spectrum fungicide, calophycin, has been isolated from Calothrix fusca EU-10-1, a terrestrial blue-green alga belonging to Nostocaceae, and identified to be a cyclic decapeptide, cyclic (L-Ala-D-Asp-L-Asn-L-Gln-Gly-L-Arg-L-N-MeAsn-L-Pro-(2R,3R,4S)-Hamp-L-Val), where Hamp is a (2R,3R,4S)-3-amino-2-hydroxy-4-methylpalmitic acid unit and MeAsn is an N-methylasparagine residue. Its total structure, including absolute stereochemistry, was determined by a combination of spectral and chemical studies, including synthesis of the unusual beta-amino acid Hamp.

  DOI：

  10.1021/jo00030a013

文献信息

• Structures of puwainaphycins A–E
  作者：John M. Gregson、Jian-Lu Chen、Gregory M.L. Patterson、Richard E. Moore

  DOI：10.1016/s0040-4020(01)92264-1

  日期：1992.1

  Puwainaphycins A-E, one of which (C) is a potent cardioactive agent in isolated mouse atria, are cyclic decapeptides that have been isolated from a terrestrial blue-green alga Anabaena sp. BQ- 16-1. The structures of puwainaphycins A-E, including most of the stereochemical features, have been elucidated by a combination of spectral and chemical methods.