(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-di-O-mesyl-1,6-thia-D-mannitol | 347837-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-di-O-mesyl-1,6-thia-D-mannitol
• 英文别名: [(3S,4R,5R,6S)-5-methylsulfonyloxy-3,6-bis(phenylmethoxy)thiepan-4-yl] methanesulfonate
• CAS: 347837-93-8
• 化学式: C₂₂H₂₈O₈S₃
• 分子量: 516.658
• InChiKey: ODMXVCRTKYCHDC-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 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-2,5-di-O-benzyl-3,4-di-O-mesyl-1,6-thia-D-mannitol 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以85%的产率得到(-)-(3S,4R,5R,6S)-4,5-diazido-3,6-di-O-benzylthiepane
  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-anhydro-3,4-O-isopropylidene-1-thio-D-mannitol 在 吡啶 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 48.5h， 生成 (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-di-O-mesyl-1,6-thia-D-mannitol
  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 glycosidase inhibition of new enantiopure 2,3-diamino conduritols
  作者：Antonio Arcelli、Vanda Cerè、Francesca Peri、Salvatore Pollicino、Alfredo Ricci

  DOI：10.1016/s0040-4020(01)00188-0

  日期：2001.4

  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.