2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate | 438216-13-8

• 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-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate
• 英文别名: [(2S,4aR,6S,7R,8S,8aS)-8-[(2S)-3-cyclohexyl-1-methoxy-1-oxopropan-2-yl]oxy-2-phenyl-6-pyridin-2-ylsulfanylcarbonyloxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 438216-13-8
• 化学式: C₃₆H₃₉NO₁₀S
• 分子量: 677.772
• InChiKey: ZXNYEHUHHVSDOU-LFNMIPMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate 在 lithium hydroxide 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 50.5h， 生成 (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
• 作为产物：
  描述：

  Di-S-(2-pyridyl) dithiocarbonate 、 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-D-galactopyranose 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate
  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.