2-(trimethylsilyl)ethyl O-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranoside | 438216-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-(trimethylsilyl)ethyl O-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranoside
• 英文别名: methyl (2S)-2-[[(2S,4aR,6R,7R,8R,8aS)-7-hydroxy-2-phenyl-6-(2-trimethylsilylethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3-cyclohexylpropanoate
• CAS: 438216-09-2
• 化学式: C₂₈H₄₄O₈Si
• 分子量: 536.738
• InChiKey: HHSSNUWIDDLBTA-FZHBBNGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl O-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Benzoic acid (3R,4S,5S,6R)-4-((S)-2-cyclohexyl-1-methoxycarbonyl-ethoxy)-2,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester
  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.