N-α-Z-O-tosyl-threonine methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-α-Z-O-tosyl-threonine methyl ester
• 英文别名: Methyl 3-(4-methylphenyl)sulfonyloxy-2-(phenylmethoxycarbonylamino)butanoate
• 化学式: C₂₀H₂₃NO₇S
• 分子量: 421.471
• InChiKey: VCMLJDBTYFLSID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-苄氧羰酰基-L-苏氨酸甲酯 、 对甲苯磺酰氯 在 吡啶 作用下， 以90%的产率得到N-α-Z-O-tosyl-threonine methyl ester
  参考文献：
  名称：

  DEHYDRATION OF THREONINE ESTERS DURING TOSYLATION

  摘要：

  Tosylation of N-alpha -protected threonine methyl-and benzyl esters was investigated. Depending on the protecting groups, the composition of the reaction mixtures showed different ratio between O-tosyl-and dehydrothreonine derivatives. The latter was formed exclusively in case of N-alpha -Fmoc-threonine benzyl ester.

  DOI：

  10.1081/scc-100107012

文献信息

• DEHYDRATION OF THREONINE ESTERS DURING TOSYLATION
  作者：Csaba Somlai、Sándor Lovas、Péter Forgó、Richard F. Murphy、Botond Penke

  DOI：10.1081/scc-100107012

  日期：2001.1

  Tosylation of N-alpha -protected threonine methyl-and benzyl esters was investigated. Depending on the protecting groups, the composition of the reaction mixtures showed different ratio between O-tosyl-and dehydrothreonine derivatives. The latter was formed exclusively in case of N-alpha -Fmoc-threonine benzyl ester.