O-(3-O-acetyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide | 1132975-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3-O-acetyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide
• 英文别名: [(2R,4aR,6S,7S,8R,8aR)-6-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-6-azido-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 1132975-35-9
• 化学式: C₇₁H₆₇N₅O₁₈
• 分子量: 1278.34
• InChiKey: WJQDEXSZJZQGLJ-HTMBMCPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  94
• 可旋转键数：
  24
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  237
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  [(2R,4aR,6S,7R,8S,8aR)-6-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-6-azido-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenyl-7-(trifluoromethylsulfonyloxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 O-(2-O-acetyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide 、 O-(3-O-acetyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide
  参考文献：
  名称：

  N-聚糖核心三糖的便捷合成

  摘要：

  描述了N-聚糖的核心三糖的方便合成。进行三个单糖结构单元的正交一锅糖基化反应以提供β-葡萄糖基壳二糖，然后通过分子内差向异构化β-葡萄糖苷的C-2位将其转化为β-甘露糖基壳二糖。遵循4，6 - O-亚苄基保护的1，2-原酸酯策略，制备了具有分化的2，3-OH的关键葡糖基供体7c。

  DOI：

  10.1016/j.tetlet.2011.04.060

文献信息

• Convenient Synthesis of an <i>N</i>-Glycan Octasaccharide of the Bisecting Type
  作者：Guangfa Wang、Wei Zhang、Zhichao Lu、Peng Wang、Xiuli Zhang、Yingxia Li

  DOI：10.1021/jo900016j

  日期：2009.3.20

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.