5-N-Phthalyl-2,3,4-tri-O-benzyl-L-ribose | 138924-93-3

• 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-ribose
• 英文别名: (2S,3S,4S)-5-(1,3-dioxoisoindol-2-yl)-2,3,4-tris(phenylmethoxy)pentanal
• CAS: 138924-93-3
• 化学式: C₃₄H₃₁NO₆
• 分子量: 549.623
• InChiKey: QBLXBKBSCOFVGR-QAXCHELISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  41.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 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 、 二甲基硫 、 臭氧 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 36.17h， 生成 5-N-Phthalyl-2,3,4-tri-O-benzyl-L-ribose
  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 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.