(-)-1,6-dideoxy-3,4-methanesulfonyl-2,5-di-O-methyl-1,6-thia-D-sorbitol | 63700-02-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (-)-1,6-dideoxy-3,4-methanesulfonyl-2,5-di-O-methyl-1,6-thia-D-sorbitol
• 英文别名: (+)-1,6-anhydrous-4,5-di-O-methanesulfonyl-3,6-dimethoxy-1,6-thia-L-iditol；[(3R,4R,5R,6R)-3,6-dimethoxy-5-methylsulfonyloxythiepan-4-yl] methanesulfonate
• CAS: 63700-02-7
• 化学式: C₁₀H₂₀O₈S₃
• 分子量: 364.462
• InChiKey: VWIPREWLFZTZHT-AXTSPUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 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：
  147
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (-)-1,6-dideoxy-3,4-methanesulfonyl-2,5-di-O-methyl-1,6-thia-D-sorbitol 在 sodium azide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 (-)-(3R,4R,5R,6S)-2,5-diazido-3,6-dimethoxythiepane-S,S-oxide
  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
• 作为产物：
  描述：

  1,6-Anhydo-2,5-di-O-methyl-1(6)-thio-L-idit 、 甲基磺酰氯 在 吡啶 作用下， 生成 (-)-1,6-dideoxy-3,4-methanesulfonyl-2,5-di-O-methyl-1,6-thia-D-sorbitol
  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

文献信息

• Synthesis and biological activity of the (−)-(2R,3S,4S)-3-azido-4-methoxy-2-(1′S-methoxy-2′-azido)ethyl-thiolane
  作者：Antonio Arcelli、Vanda Cerè、Francesca Peri、Salvatore Pollicino、Piera Sabatino

  DOI：10.1016/s0957-4166(00)00071-9

  日期：2000.4

  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.