(2R,3r)-(2-n-十二酰)-氨基-1-甲基硫代-3-羟基壬烷 | 144474-37-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (2R,3r)-(2-n-十二酰)-氨基-1-甲基硫代-3-羟基壬烷
• 英文名称: (erythro)-2-(N-Lauroyl)-amino-1-methylthio-3-hydroxy-nonane
• 英文别名: Msdh-C；N-[(2R,3R)-3-hydroxy-1-methylsulfanylnonan-2-yl]dodecanamide
• CAS: 144474-37-3
• 化学式: C₂₂H₄₅NO₂S
• 分子量: 387.671
• InChiKey: FWXRYYWKKSLFEH-LEWJYISDSA-N

物化性质

• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3r)-(2-n-十二酰)-氨基-1-甲基硫代-3-羟基壬烷 、 碘甲烷 以 乙醇 为溶剂， 反应 24.0h， 以91%的产率得到(erythro)-1-Dimethylsulfonium-2-dodecanoylamino-3-hydroxy-nonane iodide
  参考文献：
  名称：

  Synthesis of potential inhibitors of the glycosphingolipid biosynthesis

  摘要：

  A synthesis of ceramide analogs 6 and 7 is reported here starting from L-cysteine. Alkylation of 2 and subsequent reduction of the intermediate formed ketone 3 afforded the diastereomeric alcohols 4. Deprotection and acylation of 4 lead to the desired product 6 which is converted to the sulfonium salt 7. Compound 6 is a powerful inhibitor of the glycosphingolipid biosynthesis.

  DOI：

  10.1016/s0040-4020(01)90177-2
• 作为产物：
  描述：

  ((R)-1-Methylsulfanylmethyl-2-oxo-octyl)-carbamic acid tert-butyl ester 在 盐酸 、 sodium tetrahydroborate 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醚 、 异丙醇 为溶剂， 反应 16.0h， 生成 (2R,3r)-(2-n-十二酰)-氨基-1-甲基硫代-3-羟基壬烷
  参考文献：
  名称：

  Synthesis of potential inhibitors of the glycosphingolipid biosynthesis

  摘要：

  A synthesis of ceramide analogs 6 and 7 is reported here starting from L-cysteine. Alkylation of 2 and subsequent reduction of the intermediate formed ketone 3 afforded the diastereomeric alcohols 4. Deprotection and acylation of 4 lead to the desired product 6 which is converted to the sulfonium salt 7. Compound 6 is a powerful inhibitor of the glycosphingolipid biosynthesis.

  DOI：

  10.1016/s0040-4020(01)90177-2

文献信息

• Synthesis of potential inhibitors of the glycosphingolipid biosynthesis
  作者：Gerald Brenner-Weiß、Athanassios Giannis、Konrad Sandhoff

  DOI：10.1016/s0040-4020(01)90177-2

  日期：1992.7

  A synthesis of ceramide analogs 6 and 7 is reported here starting from L-cysteine. Alkylation of 2 and subsequent reduction of the intermediate formed ketone 3 afforded the diastereomeric alcohols 4. Deprotection and acylation of 4 lead to the desired product 6 which is converted to the sulfonium salt 7. Compound 6 is a powerful inhibitor of the glycosphingolipid biosynthesis.