2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester | 188636-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester
• CAS: 188636-79-5
• 化学式: C₆₀H₇₀O₁₅
• 分子量: 1031.21
• InChiKey: MUDSHISGEGBQCM-XVBJBXPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.99
• 重原子数：
  75.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  154.13
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 为溶剂， 反应 26.0h， 生成 2-(2-{(2R,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3-yloxy}-ethyl)-malonic acid
  参考文献：
  名称：

  Pitfalls in the synthesis and biological evaluation of sialyl-LewisX mimetics as potential selectin antagonists

  摘要：

  The lower molecular weight analog 12 of sialyl Lewis(X) was prepared and effected equal binding affinity to E- and P-selectin compared to the parent tetrasaccharide. If 12 was prepared using acidic ion exchange resins, false positive test were produced, especially binding to P-selectin seemed to be considerably enhanced. Traces of polyanions released from the resins which are difficult to detect by routine analysis were identified to be highly potent selectin inhibitors, probably by their action on a non-carbohydrate binding site. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01178-7
• 作为产物：
  描述：

  [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1R,2R)-2-hydroxycyclohexyl]oxyoxan-2-yl]methyl acetate 在 Wilkinson's catalyst 、 二苯并-18-冠醚-6 、 1,2-二溴四氯乙烷 、 4 A molecular sieve 、 四丁基溴化铵 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 、 copper(ll) bromide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 92.0h， 生成 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester
  参考文献：
  名称：

  Pitfalls in the synthesis and biological evaluation of sialyl-LewisX mimetics as potential selectin antagonists

  摘要：

  The lower molecular weight analog 12 of sialyl Lewis(X) was prepared and effected equal binding affinity to E- and P-selectin compared to the parent tetrasaccharide. If 12 was prepared using acidic ion exchange resins, false positive test were produced, especially binding to P-selectin seemed to be considerably enhanced. Traces of polyanions released from the resins which are difficult to detect by routine analysis were identified to be highly potent selectin inhibitors, probably by their action on a non-carbohydrate binding site. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01178-7