methyl O-(4,6-O-benzylidene-2-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl)-(1->3)-O-[(2,3,4-tri-O-benzyl-β-D-arabinopyranosyl)-(1->4)]-O-(6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4,6-O-benzylidene-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 1360878-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(4,6-O-benzylidene-2-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl)-(1->3)-O-[(2,3,4-tri-O-benzyl-β-D-arabinopyranosyl)-(1->4)]-O-(6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4,6-O-benzylidene-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS: 1360878-39-2
• 化学式: C₁₁₇H₁₀₈ClNO₃₂
• 分子量: 2075.59
• InChiKey: UNDTUVHTDSZNMB-KWEGKXPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.21
• 重原子数：
  151.0
• 可旋转键数：
  38.0
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  361.32
• 氢给体数：
  0.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  methyl O-(4,6-O-benzylidene-2-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl)-(1->3)-O-[(2,3,4-tri-O-benzyl-β-D-arabinopyranosyl)-(1->4)]-O-(6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4,6-O-benzylidene-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 吡啶 、 甲醇 、 硫脲 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到methyl O-(4,6-O-benzylidene-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-O-[(2,3,4-tri-O-benzyl-β-D-arabinopyranosyl)-(1->4)]-O-(6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4,6-O-benzylidene-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a sulfonic acid mimetic of the sulfated Lewis A pentasaccharide

  摘要：

  The first sulfonic acid mimetic of the sulfated Lewis A pentasaccharide in which the natural L-fucose unit is replaced by a D-arabinose ring was synthesized. Formation of the sulfonic acid moiety at a pentasaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the terminal D-galactose residue and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be obtained by double nucleophilic substitutions; efficient formation of the gulo-triflate derivatives required low-power microwave (MW) activation. Oxidation of the acetylthio group was carried out using Oxone in the presence of acetic acid. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.015
• 作为产物：
  描述：

  ethyl 6-O-benzyl-3-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-4-O-(2,3,4-tri-O-benzyl-β-D-arabinopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 、 methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-O-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以45%的产率得到methyl O-(4,6-O-benzylidene-2-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl)-(1->3)-O-[(2,3,4-tri-O-benzyl-β-D-arabinopyranosyl)-(1->4)]-O-(6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4,6-O-benzylidene-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a sulfonic acid mimetic of the sulfated Lewis A pentasaccharide

  摘要：

  The first sulfonic acid mimetic of the sulfated Lewis A pentasaccharide in which the natural L-fucose unit is replaced by a D-arabinose ring was synthesized. Formation of the sulfonic acid moiety at a pentasaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the terminal D-galactose residue and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be obtained by double nucleophilic substitutions; efficient formation of the gulo-triflate derivatives required low-power microwave (MW) activation. Oxidation of the acetylthio group was carried out using Oxone in the presence of acetic acid. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.015