(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-3-O-benzoyl-6-O-benzyl-1,2,-dideoxy-D-glucopyranose | 438216-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-3-O-benzoyl-6-O-benzyl-1,2,-dideoxy-D-glucopyranose
• 英文别名: [(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] benzoate
• CAS: 438216-16-1
• 化学式: C₄₇H₅₀O₉
• 分子量: 758.909
• InChiKey: PAQVDKUMCBMCGS-HETVQTMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-3-O-benzoyl-6-O-benzyl-1,2,-dideoxy-D-glucopyranose 在 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 (2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-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：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 4 A molecular sieve 、 三乙胺 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-3-O-benzoyl-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.