2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-((3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yloxy)-tetrahydro-pyran-2-ylmethyl ester | 218792-71-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-((3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS: 218792-71-3
• 化学式: C₃₃H₄₅NO₁₃
• 分子量: 663.719
• InChiKey: NHJVTLRCNNZRNV-MJBBOZQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  173.43
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-((3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yloxy)-tetrahydro-pyran-2-ylmethyl ester 在 palladium dihydroxide sodium hydroxide 、 四丁基溴化铵 、 氢气 、 sodium methylate 、 二正丁基氧化锡 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 {(2R,3S,4S,5R,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-[(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]-tetrahydro-pyran-4-yloxy}-acetic acid
  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：

  2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester 在 吡啶 、 氢氟酸 作用下， 反应 4.0h， 以75%的产率得到2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-((3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yloxy)-tetrahydro-pyran-2-ylmethyl 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