5-N-Phthalyl-2,3,4-tri-O-benzyl-L-arabinose diethyl dithioacetal | 138925-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-N-Phthalyl-2,3,4-tri-O-benzyl-L-arabinose diethyl dithioacetal
• CAS: 138925-01-6
• 化学式: C₃₈H₄₁NO₅S₂
• 分子量: 655.879
• InChiKey: AHNFFJUXAWVTPK-GVBYMILNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  46.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-N-Phthalyl-2,3,4-tri-O-benzyl-L-arabinose diethyl dithioacetal 在 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 、 双氧水 、 碳酸氢钠 、 三乙胺 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， -78.0~50.0 ℃ 、8.62 MPa 条件下， 反应 0.5h， 生成 8a-epicastanospermine
  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
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 5-N-Phthalyl-2,3,4-tri-O-benzyl-L-arabinose diethyl dithioacetal
  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