methyl 2-[(2R,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-2-dimethoxyphosphorylacetate | 438216-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[(2R,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-2-dimethoxyphosphorylacetate
• CAS: 438216-07-0
• 化学式: C₃₇H₅₁O₁₁PSi
• 分子量: 730.865
• InChiKey: QBFCFPKMZXCJQQ-DXPJXCCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  环己烷基甲醛 、 methyl 2-[(2R,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-2-dimethoxyphosphorylacetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 2-(trimethylsilyl)ethyl O-2,4,6-tri-O-benzyl-3-O-[(Z)-1-(methoxycarbonyl)-2-cyclohexylethylen-1-oxy]-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl O-2,4,6-tri-O-benzyl-3-O-[(E)-1-(methoxycarbonyl)-2-cyclohexylethylen-1-oxy]-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Potent Antagonist of E-Selectin

  摘要：

  A synthesis of an antagonist of E-selectin previously reported by a group at Novartis Pharma in Basel is described. An important feature involves the formation of an ether linkage based on a Rh-II-catalyzed reaction. Stereocontrolled glycosylations rely on the anomeric activation of 2-pyridylthio carbonate as leaving group for the attachment of beta-D-galactopyranosyl and alpha-L-fucopyranosyl units on a common 1,5-anhydro D-glucitol scaffold.

  DOI：

  10.1021/jo0110956
• 作为产物：
  描述：

  三甲基膦酰基乙酸酯 在 dirhodium tetraacetate 、 potassium tert-butylate 作用下， 以 甲苯 、 苯 为溶剂， 反应 8.0h， 生成 methyl 2-[(2R,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-2-dimethoxyphosphorylacetate
  参考文献：
  名称：

  Synthesis of a Potent Antagonist of E-Selectin

  摘要：

  A synthesis of an antagonist of E-selectin previously reported by a group at Novartis Pharma in Basel is described. An important feature involves the formation of an ether linkage based on a Rh-II-catalyzed reaction. Stereocontrolled glycosylations rely on the anomeric activation of 2-pyridylthio carbonate as leaving group for the attachment of beta-D-galactopyranosyl and alpha-L-fucopyranosyl units on a common 1,5-anhydro D-glucitol scaffold.

  DOI：

  10.1021/jo0110956

文献信息

• Synthesis of a Potent Antagonist of E-Selectin
  作者：Stephen Hanessian、Vincent Mascitti、Olivier Rogel

  DOI：10.1021/jo0110956

  日期：2002.5.1

  A synthesis of an antagonist of E-selectin previously reported by a group at Novartis Pharma in Basel is described. An important feature involves the formation of an ether linkage based on a Rh-II-catalyzed reaction. Stereocontrolled glycosylations rely on the anomeric activation of 2-pyridylthio carbonate as leaving group for the attachment of beta-D-galactopyranosyl and alpha-L-fucopyranosyl units on a common 1,5-anhydro D-glucitol scaffold.