(S)-2-((2S,4aR,6R,7R,8R,8aS)-6-{(1R,2R)-2-[(2R,3S,4R,5R,6S)-6-(2-Allyloxycarbonyl-ethyl)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy]-cyclohexyloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-3-phenyl-propionic acid benzyl ester | 198828-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-((2S,4aR,6R,7R,8R,8aS)-6-{(1R,2R)-2-[(2R,3S,4R,5R,6S)-6-(2-Allyloxycarbonyl-ethyl)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy]-cyclohexyloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-3-phenyl-propionic acid benzyl ester
• CAS: 198828-34-1
• 化学式: C₆₇H₇₄O₁₅
• 分子量: 1119.32
• InChiKey: NWSRLAZXNOEGHL-YTSHJLEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.26
• 重原子数：
  82.0
• 可旋转键数：
  26.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  165.13
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((2S,4aR,6R,7R,8R,8aS)-6-{(1R,2R)-2-[(2R,3S,4R,5R,6S)-6-(2-Allyloxycarbonyl-ethyl)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy]-cyclohexyloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-3-phenyl-propionic acid benzyl ester 在 吗啉 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-((2S,4aR,6R,7S,8R,8aS)-7-Hydroxy-2-phenyl-6-{(1R,2R)-2-[(2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-(2-carboxy-ethyl)-tetrahydro-pyran-2-yloxy]-cyclohexyloxy}-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-3-phenyl-propionic acid benzyl ester
  参考文献：
  名称：

  Design and synthesis of a macrocyclic E-Selectin antagonist

  摘要：

  The macrocyclic sialyl Lewis(x) mimic 2 has been synthesized starting from L-galactose. The core of 2 is extremely rigid as indicated by molecular modelling. This compound functions as a structural probe for exploring the spatial orientation of the functional groups involved in binding to E-Selectin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10041-5
• 作为产物：
  描述：

  2-trimethylsilylethyl 2,3,4-tri-O-benzyl-β-L-galactopyranoside 在 platinum(IV) oxide lithium hydroxide 、 草酰氯 、 草酰溴 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基溴化铵 、 氢气 、 sodium methylate 、 二正丁基氧化锡 、 caesium carbonate 、 DMTST 、 三乙胺 、 cesium fluoride 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成 (S)-2-((2S,4aR,6R,7R,8R,8aS)-6-{(1R,2R)-2-[(2R,3S,4R,5R,6S)-6-(2-Allyloxycarbonyl-ethyl)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy]-cyclohexyloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-3-phenyl-propionic acid benzyl ester
  参考文献：
  名称：

  Design and synthesis of a macrocyclic E-Selectin antagonist

  摘要：

  The macrocyclic sialyl Lewis(x) mimic 2 has been synthesized starting from L-galactose. The core of 2 is extremely rigid as indicated by molecular modelling. This compound functions as a structural probe for exploring the spatial orientation of the functional groups involved in binding to E-Selectin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10041-5