(3R,4R,5R)-3-(Benzyloxycarbonyl-phenyl-methoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid benzyl ester | 218792-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5R)-3-(Benzyloxycarbonyl-phenyl-methoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS: 218792-66-6
• 化学式: C₇₁H₇₃NO₁₂Si
• 分子量: 1160.45
• InChiKey: BSOCBNGJZZSMOM-KRCVUQITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.87
• 重原子数：
  85.0
• 可旋转键数：
  24.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  137.52
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3-(Benzyloxycarbonyl-phenyl-methoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid benzyl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 反应 6.0h， 以90%的产率得到[(3R,4R,5R)-5-Hydroxymethyl-2-oxo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyrrolidin-3-yloxy]-phenyl-acetic acid benzyl ester
  参考文献：
  名称：

  Exploration of β-turn scaffolding motifs as components of sialyl LeX mimetics and their relevance to P-selectin

  摘要：

  Monocyclic and bicyclic lactam units representing P-turn surrogates were incorporated into a sialyl Le(X) structure by replacement of the natural sugar components. I;ow micromolar activity was found in a new P-selectin binding assay.(C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00500-9
• 作为产物：
  描述：

  (2R,3R,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester 在 dirhodium tetraacetate 、 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (3R,4R,5R)-3-(Benzyloxycarbonyl-phenyl-methoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Exploration of β-turn scaffolding motifs as components of sialyl LeX mimetics and their relevance to P-selectin

  摘要：

  Monocyclic and bicyclic lactam units representing P-turn surrogates were incorporated into a sialyl Le(X) structure by replacement of the natural sugar components. I;ow micromolar activity was found in a new P-selectin binding assay.(C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00500-9