(2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose | 438216-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose
• 英文别名: (2S)-2-[[(2S,4aR,6R,7R,8S,8aS)-7-benzoyloxy-6-[(2R,3S,4R)-3-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)oxan-4-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3-cyclohexylpropanoic acid
• CAS: 438216-19-4
• 化学式: C₆₉H₇₈O₁₆
• 分子量: 1163.37
• InChiKey: VTEVXDNEKAYFQJ-ZDIQYNPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  85
• 可旋转键数：
  26
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  174
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose 在 palladium dihydroxide 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 42.0h， 生成 (3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[α-L-fucopyranosyl)-O-(1->4)]-1,2-dideoxy-D-glucopyranose
  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：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 lithium hydroxide 、 4 A molecular sieve 、 sodium methylate 、 sodium hydride 、 三乙胺 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 98.5h， 生成 (2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose
  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.