[(3S,6S,8S,8aS)-8-Benzyloxy-5-oxo-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yloxy]-phenyl-acetic acid methyl ester | 218792-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3S,6S,8S,8aS)-8-Benzyloxy-5-oxo-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yloxy]-phenyl-acetic acid methyl ester
• CAS: 218792-64-4
• 化学式: C₅₂H₅₇NO₁₀
• 分子量: 856.025
• InChiKey: VCBQONHSTHLRFY-MHZJJUCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.15
• 重原子数：
  63.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111.22
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(3S,6S,8S,8aS)-8-Benzyloxy-5-oxo-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yloxy]-phenyl-acetic acid methyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以100%的产率得到[(3S,6S,8S,8aS)-8-Hydroxy-5-oxo-3-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yloxy]-phenyl-acetic acid methyl 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：

  Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester 在 dirhodium tetraacetate 、 四丁基溴化铵 、 sodium methylate 、 copper(ll) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 [(3S,6S,8S,8aS)-8-Benzyloxy-5-oxo-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yloxy]-phenyl-acetic acid methyl 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