(-)-1,6-dideoxy-3,4-methanesulfonyl-2,5-di-O-methyl-1,6-thia-D-sorbitol-S,S-oxide | 347837-86-9

• 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-S,S-oxide
• 英文别名: [(3R,4R,5R,6S)-3,6-dimethoxy-5-methylsulfonyloxy-1,1-dioxothiepan-4-yl] methanesulfonate
• CAS: 347837-86-9
• 化学式: C₁₀H₂₀O₁₀S₃
• 分子量: 396.461
• InChiKey: PGHMTVHRLZDHCQ-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  23
• 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：
  165
• 氢给体数：
  0
• 氢受体数：
  10

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-S,S-oxide 在 氢氧化钾 、 sodium azide 、 sodium hydride 作用下， 以 四氯化碳 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 21.0h， 生成 (+)-(1S,2R,3R,4R)-2,3-diazido-1,4-dimethoxycyclohex-5-ene
  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 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (-)-1,6-dideoxy-3,4-methanesulfonyl-2,5-di-O-methyl-1,6-thia-D-sorbitol-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