ethyl 4,6-O-benzylidene-2,3-di-O-(chloroacetyl)-1-thio-β-D-glucopyranoside | 1132975-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-O-benzylidene-2,3-di-O-(chloroacetyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-7-(2-chloroacetyl)oxy-6-ethylsulfanyl-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2-chloroacetate
• CAS: 1132975-32-6
• 化学式: C₁₉H₂₂Cl₂O₇S
• 分子量: 465.351
• InChiKey: YSKWBNFWGKVIQB-LPSXLJMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-O-benzylidene-2,3-di-O-(chloroacetyl)-1-thio-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.03h， 生成 4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl 2-chloroorthoacetate)
  参考文献：
  名称：

  Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-d-glucopyranosylorthoesters strategy

  摘要：

  A facile and efficient method to differentiate the 2,3-diols of glucopyranosides based on 1,2-orthoesters strategy was developed. Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters. When treated with HCl aqueous solution and followed with Et3N, differentiation of the 2,3-diols was efficiently achieved along with the generation of a convertible anomeric hydroxyl group. In addition, an easy and practical method based on NOE was proposed to determine whether the 1,2-orthoesters were endo-type or exo-type. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.008
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 、 氯乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到ethyl 4,6-O-benzylidene-2,3-di-O-(chloroacetyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  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.

  DOI：

  10.1021/jo900016j

文献信息

• Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-d-glucopyranosylorthoesters strategy
  作者：Guangfa Wang、Zhichao Lu、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li

  DOI：10.1016/j.carres.2011.08.008

  日期：2011.11

  A facile and efficient method to differentiate the 2,3-diols of glucopyranosides based on 1,2-orthoesters strategy was developed. Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters. When treated with HCl aqueous solution and followed with Et3N, differentiation of the 2,3-diols was efficiently achieved along with the generation of a convertible anomeric hydroxyl group. In addition, an easy and practical method based on NOE was proposed to determine whether the 1,2-orthoesters were endo-type or exo-type. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.