(S)-3-octadecanoyl-4-benzyloxazolidin-2-one | 160186-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-3-octadecanoyl-4-benzyloxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-octadecanoyl-1,3-oxazolidin-2-one
• CAS: 160186-21-0
• 化学式: C₂₈H₄₅NO₃
• 分子量: 443.67
• InChiKey: BLEIXOHOGJSHKU-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-octadecanoyl-4-benzyloxazolidin-2-one 在 lithium hydroxide 、 水 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 2R-Hexadecyl-succinic acid-4-tert-butyl ester
  参考文献：
  名称：

  Inhibition of Matrix Metalloproteinases: An examination of the S1′ pocket

  摘要：

  Peptidomimetic carboxylate- and hydroxamate-based inhibitors of matrix metalloproteinases containing extended P1' groups have been prepared. Potent inhibition and good selectivity for MMP-2 has been observed for the compounds produced. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00602-6
• 作为产物：
  描述：

  (S)-4-苄基-2-唑烷酮 、 十八烷酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以80%的产率得到(S)-3-octadecanoyl-4-benzyloxazolidin-2-one
  参考文献：
  名称：

  Synthesis of the 4 possible stereoisomers of 3-O-stearoyl C36-corynomycolic acid and derived lipopeptides.

  摘要：

  A short synthesis of 3-O-stearoyl (S,R), (R,S), (S,S) and (R,R) C-36-corynomycolic acids is described. Coupling through a spacer to lysyl-lysyl-lysyl-lysine afforded the corresponding water soluble lipopeptides which showed antagonistic activity against LPS activation of macrophages in vitro.

  DOI：

  10.1016/s0040-4020(01)80646-3

文献信息

• A Convenient Synthesis of Chiral β³-Amino Acids
  作者：Tushar K. Chakraborty、Animesh Ghosh

  DOI：10.1055/s-2002-35608

  日期：——

  A novel method for the synthesis of chiral β3-amino acids is developed where the acid functionality was built by oxidative cleavage of an α-allylic group that was introduced by Evans’ asymmetric alkylation of an appropriate acid substrate and the amino part came from the amide of the original carboxyl group following a modified Hofmann rearrangement reaction.

  开发了一种合成手性β3-氨基酸的新方法，其中酸功能团是通过氧化断裂引入的α-烯丙基，该基团由Evans不对称烷基化适当的酸底物引入，而氨基部分则来自原始羧基的酰胺，经过改良的Hofmann重排反应后形成。
• Synthesis of chiral α-amino acids
  作者：Tushar K Chakraborty、Animesh Ghosh

  DOI：10.1016/s0040-4039(02)02433-4

  日期：2002.12

  A novel method for the synthesis of chiral alpha-amino acids has been developed where the acid functionality was constructed by oxidizing a hydroxymethyl group introduced by Evans' method in the alpha-position of an appropriate acid substrate and the amino part came from the amide of the original carboxyl group following a modified Hofmann rearrangement reaction. (C) 2002 Published by Elsevier Science Ltd.