(-)-(2R,3S,4S)-3-azido-4-methoxy-2-(1'S-methoxy-2'-azido)ethyl-thiolane | 283584-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (-)-(2R,3S,4S)-3-azido-4-methoxy-2-(1'S-methoxy-2'-azido)ethyl-thiolane
• 英文别名: (2R,3S,4S)-3-azido-2-[(1S)-2-azido-1-methoxyethyl]-4-methoxythiolane
• CAS: 283584-91-8
• 化学式: C₈H₁₄N₆O₂S
• 分子量: 258.304
• InChiKey: OZFUHZCQLIYGRR-YWIQKCBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3S,4S)-3-azido-4-methoxy-2-(1'S-methoxy-2'-azido)ethyl-thiolane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以97%的产率得到(-)-(2R,3S,4S)-3-amino-4-methoxy-2-(1'S-methoxy-2'-amino)ethyl-thiolane
  参考文献：
  名称：

  Synthesis and biological activity of the (−)-(2R,3S,4S)-3-azido-4-methoxy-2-(1′S-methoxy-2′-azido)ethyl-thiolane

  摘要：

  A stereospecific ring contraction reaction, promoted by NaN3, was detected starting from a thiepane derivative obtained from D-sorbitol, an inexpensive alcohol sugar. The major polyfunctionalized thiolane derivative obtained was investigated as a potential glycosidase inhibitor. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00071-9
• 作为产物：
  描述：

  1,6-Anhydo-2,5-di-O-methyl-1(6)-thio-L-idit 在 吡啶 、 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 生成 (-)-(2R,3S,4S)-3-azido-4-methoxy-2-(1'S-methoxy-2'-azido)ethyl-thiolane
  参考文献：
  名称：

  Synthesis and glycosidase inhibition of new enantiopure 2,3-diamino conduritols

  摘要：

  A new 2,3-diamino conduritol, isoster of conduritol F, was obtained starting from D-sorbitol. In the synthetic sequence an unprecedented transannular cyclization led, as a side product, to a bicyclic compound bearing a cyclopropyl ring. The synthesis of the completely deprotected 2,3-diamino conduritol, isoster of conduritol B, was devised via the intermediate O-benzylation of the OH groups. The O-methylated and deprotected 2,3-diamino conduritols were evaluated as inhibitors of alpha- and beta -glucosidase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00188-0