3,4,5-tri-O-benzyl-1,2-dideoxy-L-ribo-hex-1-enitol | 139014-28-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,4,5-tri-O-benzyl-1,2-dideoxy-L-ribo-hex-1-enitol
• 英文别名: (2S,3R,4R)-2,3,4-Tris(benzyloxy)-hex-5-en-1-ol；(2S,3R,4R)-2,3,4-tris(phenylmethoxy)hex-5-en-1-ol
• CAS: 139014-28-1
• 化学式: C₂₇H₃₀O₄
• 分子量: 418.533
• InChiKey: NTOSGFLXZNOARL-KWXIBIRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,5-tri-O-benzyl-1,2-dideoxy-L-ribo-hex-1-enitol 在 sodium iodide 作用下， 以 吡啶 、 六甲基磷酰三胺 为溶剂， 生成 3,4,5-tri-O-benzyl-1,2,6-trideoxy-6-iodo-L-ribo-hex-1-enitol
  参考文献：
  名称：

  The Cobalt-Catalyzed Oxygenative Radical Route from Hexopyranosides to Carbapentofuranoses

  摘要：

  DOI：

  10.1002/1099-0690(200009)2000:17<3075::aid-ejoc3075>3.0.co;2-c
• 作为产物：
  描述：

  (2S,3R,4R)-1-O-Acetyl-2,3,4-tri-O-benzyladonitol 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 24.08h， 生成 3,4,5-tri-O-benzyl-1,2-dideoxy-L-ribo-hex-1-enitol
  参考文献：
  名称：

  A route to several stereoisomers of castanospermine

  摘要：

  The following three stereoisomers of castanospermine have been prepared: (1R,6R,7R,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (1), (1R,6S,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (2), and (1R,6R,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (3). Each of these compounds was synthesized via asymmetric allylation of pentose derivatives with [(Z)-gamma-(methoxymethoxy)allyl]diisopinocampheylborane, an approach which is, in principle, suitable for preparations of a total of eight stereoisomers of castanospermine. Compounds 1-3 were tested as possible inhibitors of various glycosidase enzymes and for anti-HIV-1 activity in cell cultures. They are very poor inhibitors of glycosidase enzymes; however, preliminary tests indicate indolizidines 1 and 3 have weak but significant anti-HIV activities.

  DOI：

  10.1021/jo00030a014

文献信息

• A New Synthesis of Carbapentofuranoses from Carbohydrates
  作者：Jérôme Désiré、Jacques Prandi

  DOI：10.1016/s0040-4039(97)01395-6

  日期：1997.9

  Carbafuranosides were synthesized in one step from various O-protected 1,2,6-trideoxydiodo-hex-1-enitols by cobalt catalyzed 5-exo radical-cyclization under molecular oxygen. Yields were fair to good with interesting selectivities. (C) 1997 Elsevier Science Ltd.
• The Cobalt-Catalyzed Oxygenative Radical Route from Hexopyranosides to Carbapentofuranoses
  作者：Jérôme Désiré、Jacques Prandi

  DOI：10.1002/1099-0690(200009)2000:17<3075::aid-ejoc3075>3.0.co;2-c

  日期：2000.9
• A route to several stereoisomers of castanospermine
  作者：Kevin Burgess、David A. Chaplin、Ian Henderson、Y. T. Pan、Alan D. Elbein

  DOI：10.1021/jo00030a014

  日期：1992.2

  The following three stereoisomers of castanospermine have been prepared: (1R,6R,7R,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (1), (1R,6S,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (2), and (1R,6R,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (3). Each of these compounds was synthesized via asymmetric allylation of pentose derivatives with [(Z)-gamma-(methoxymethoxy)allyl]diisopinocampheylborane, an approach which is, in principle, suitable for preparations of a total of eight stereoisomers of castanospermine. Compounds 1-3 were tested as possible inhibitors of various glycosidase enzymes and for anti-HIV-1 activity in cell cultures. They are very poor inhibitors of glycosidase enzymes; however, preliminary tests indicate indolizidines 1 and 3 have weak but significant anti-HIV activities.