[(2R,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-carbamic acid allyl ester | 1234549-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: [(2R,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-carbamic acid allyl ester
• 英文别名: prop-2-enyl N-[(2R,3S)-2-tert-butylsulfanyl-5-oxooxolan-3-yl]carbamate
• CAS: 1234549-23-5
• 化学式: C₁₂H₁₉NO₄S
• 分子量: 273.353
• InChiKey: IQBCRSCLAJNOIC-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-carbamic acid allyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (4S,5R)-4-amino-5-tert-butylsulfanyloxolan-2-one
  参考文献：
  名称：

  Synthesis of novel peptidomimetics as inhibitors of protozoan cysteine proteases falcipain-2 and rhodesain

  摘要：

  This paper describes the synthesis of novel peptidomimetics bearing a protected aspartyl aldeyde warhead leading to the thioacylals 2a,b and the acylals 3a,b. Compounds 2a and 3a proved to possess an increased antiplasmodial activity with respect to the parent molecule 1. Furthermore thioacylal 2a can be considered as a promising trypanocidal agent. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.003
• 作为产物：
  描述：

  叔丁基硫醇 、 2-allyloxycarbonylamino-4-oxobutyric acid 4-tert-butyl ester 在 四氯化钛 、 三氟乙酸 作用下， 以 氯仿 、 二氯甲烷 为溶剂， 反应 3.0h， 以0.29 mmol的产率得到[(2R,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-carbamic acid allyl ester
  参考文献：
  名称：

  Synthesis of novel peptidomimetics as inhibitors of protozoan cysteine proteases falcipain-2 and rhodesain

  摘要：

  This paper describes the synthesis of novel peptidomimetics bearing a protected aspartyl aldeyde warhead leading to the thioacylals 2a,b and the acylals 3a,b. Compounds 2a and 3a proved to possess an increased antiplasmodial activity with respect to the parent molecule 1. Furthermore thioacylal 2a can be considered as a promising trypanocidal agent. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.003

文献信息

• Synthesis of novel peptidomimetics as inhibitors of protozoan cysteine proteases falcipain-2 and rhodesain
  作者：Roberta Ettari、Maria Zappalà、Nicola Micale、Tanja Schirmeister、Christoph Gelhaus、Matthias Leippe、Astrid Evers、Silvana Grasso

  DOI：10.1016/j.ejmech.2010.04.003

  日期：2010.7

  This paper describes the synthesis of novel peptidomimetics bearing a protected aspartyl aldeyde warhead leading to the thioacylals 2a,b and the acylals 3a,b. Compounds 2a and 3a proved to possess an increased antiplasmodial activity with respect to the parent molecule 1. Furthermore thioacylal 2a can be considered as a promising trypanocidal agent. (C) 2010 Elsevier Masson SAS. All rights reserved.