(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol | 172147-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol
• CAS: 172147-75-0
• 化学式: C₃₉H₅₀O₁₁
• 分子量: 694.819
• InChiKey: RVOREMKWUXAFMS-FHACDKDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  145.53
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol 在 palladium on activated charcoal Wilkinson's catalyst 、 二苯并-18-冠醚-6 、 1,2-二溴四氯乙烷 、 氢气 、 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 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 89.0h， 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 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
• 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 4 A molecular sieve 、 四丁基溴化铵 、 sodium methylate 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol
  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

文献信息

• Development of Tools for the Design of Selectin Antagonists
  作者：Hartmuth C. Kolb、Beat Ernst

  DOI：10.1002/chem.19970031006

  日期：1997.10

  AbstractA molecular modeling tool for the rational design of E‐selectin antagonists based on the lead structure sialyl Lewisx has been developed. The binding affinity to the receptor is considerably influenced by the entropy and consequently by the antagonist's ability to place its pharmacophores in an optimal spatial arrangement, i.e., by its preorganization for binding. The computational model assesses the preorganization of a potential selectin antagonist with the aid of Monte Carlo (jumping between wells)/stochastic dynamics [MC(JBW)/SD] simulations. The model has been validated by correlating preorganization and bioactivity of several selectin antagonists. The results suggest that only preorganized compounds are likely to bind to E‐selectin.
• Ernst, Beat; Dragic, Zorica; Marti, Sébastien, Chimia, 2001, vol. 55, # 4, p. 268 - 274
  作者：Ernst, Beat、Dragic, Zorica、Marti, Sébastien、Müller, Christian、Wagner, Beatrice、Jahnke, Wolfgang、Magnani, John L.、Norman, Keith E.、Oehrlein, Reinhold、Peters, Thomas、Kolb, Hartmuth C.

  DOI：——

  日期：——
• Synthesis of sialyl lewisx mimics. Modifications of the 6-position of galactose
  作者：Rolf Bänteli、Beat Ernst

  DOI：10.1016/s0960-894x(00)00692-2

  日期：2001.2

  Seven sLe(x) mimics where the -CH2OH group of the galactose moiety is replaced by -CH2NH3+, -CH2NHAc, -CH(2)NHBz, -CH2OSO3Na, -COONa and -CONH2 have been prepared and tested for their binding affinity to E-selectin. (C) 2001 Elsevier Science Ltd. All rights reserved.