(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-isopropylidene-1,6-thia-D-mannitol | 266682-63-7

• 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-isopropylidene-1,6-thia-D-mannitol
• 英文别名: (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-D-mannitol；(3aS,4S,8S,8aS)-4,8-bis(benzyloxy)-2,2-dimethylhexahydrothiepino[4,5-d][1,3]dioxole；(3aS,4S,8S,8aS)-2,2-dimethyl-4,8-bis(phenylmethoxy)-3a,4,5,7,8,8a-hexahydrothiepino[4,5-d][1,3]dioxole
• CAS: 266682-63-7
• 化学式: C₂₃H₂₈O₄S
• 分子量: 400.539
• InChiKey: DEFWSXYMKAAKMP-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-isopropylidene-1,6-thia-D-mannitol 在 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 5.45h， 生成 (3aR,4R,7R,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-bis(phenylmethoxy)-1,3-benzodioxole
  参考文献：
  名称：

  对映体纯Conduritols的一般程序：（+）-Conduritol B和（-）-Conduritol F衍生物以及（-）-Conduritol E和F的硫介导合成。

  摘要：

  我们已经证明了简单方法的一般性，它们分别从d-甘露醇和d-山梨糖醇合成对映体纯的（+）-conduritol B和（-）-conduritol F衍生物。稍加修改后的该方法也可用于合成未保护的松露醇：（-）-松露醇E和（-）-松露醇F。

  DOI：

  10.1016/s0040-4020(00)00011-9
• 作为产物：
  描述：

  溴甲苯 、 1,6-anhydro-3,4-O-isopropylidene-1-thio-D-mannitol 在 sodium hydride 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以93%的产率得到(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-isopropylidene-1,6-thia-D-mannitol
  参考文献：
  名称：

  对映体纯Conduritols的一般程序：（+）-Conduritol B和（-）-Conduritol F衍生物以及（-）-Conduritol E和F的硫介导合成。

  摘要：

  我们已经证明了简单方法的一般性，它们分别从d-甘露醇和d-山梨糖醇合成对映体纯的（+）-conduritol B和（-）-conduritol F衍生物。稍加修改后的该方法也可用于合成未保护的松露醇：（-）-松露醇E和（-）-松露醇F。

  DOI：

  10.1016/s0040-4020(00)00011-9

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.
• Catalytic and enantioselective bromoetherification of olefinic 1,3-diols: mechanistic insight
  作者：Zhihai Ke、Chong Kiat Tan、Yi Liu、Keefe Guang Zhi Lee、Ying-Yeung Yeung

  DOI：10.1016/j.tet.2015.09.016

  日期：2016.5

  How can high enantioselectivity be achieved when the racemic background reaction proceeds at a rate comparable to that of the catalytic asymmetric reaction? We attempted to rationalize this counterin-tuitive observation by studying the effect of (1) catalyst structure, (2) temperature and addition sequence of components, (3) catalyst loading, and (4) Bronsted acid additives. In the course of our investigation, it was found that increasing the amount of catalyst used led to inhibition of the stoichiometric reaction. Olefinic 1,3-diol 1, 5 mol % of catalyst 3a, 1 equiv of MsOH, and NBS were added at low temperature in a specific sequence to provide the best performance for the enantioselective bromoetherification. (C) 2015 Elsevier Ltd. All rights reserved.
• A General Procedure to Enantiopure Conduritols: Sulfur-Mediated Synthesis of (+)-Conduritol B and (−)-Conduritol F Derivatives and of (−)-Conduritol E and F
  作者：Vanda Cerè、Giuseppe Mantovani、Francesca Peri、Salvatore Pollicino、Alfredo Ricci

  DOI：10.1016/s0040-4020(00)00011-9

  日期：2000.2

  demonstrated the generality of a simple procedure, synthesizing enantiomerically pure (+)-conduritol B and (−)-conduritol F derivatives, starting from d-mannitol and d-sorbitol, respectively. This method, slightly modified, can also be applied to the synthesis of unprotected conduritols: (−)-conduritol E and (−)-conduritol F were obtained.

  我们已经证明了简单方法的一般性，它们分别从d-甘露醇和d-山梨糖醇合成对映体纯的（+）-conduritol B和（-）-conduritol F衍生物。稍加修改后的该方法也可用于合成未保护的松露醇：（-）-松露醇E和（-）-松露醇F。