5-[(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose | 649571-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-[(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
• CAS: 649571-96-0
• 化学式: C₂₆H₄₅NO₉Si
• 分子量: 543.73
• InChiKey: DHVWANWRKMGFIQ-IWAFHXCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  101.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-[(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以74%的产率得到5-[(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)-2-hydroxy-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027
• 作为产物：
  描述：

  (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 在 咪唑 、 4-二甲氨基吡啶 、 氨 、 水 、 lithium 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 5-[(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027