methyl O-(3-S-acetyl-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 | 1360878-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(3-S-acetyl-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
• CAS: 1360878-43-8
• 化学式: C₁₁₇H₁₀₉NO₃₁S
• 分子量: 2057.21
• InChiKey: JCXSKUPCHYRYKD-CAXGARBISA-N

反应信息

• 作为反应物：
  描述：

  methyl O-(3-S-acetyl-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 在 乙二胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成
  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：

  、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以180 mg的产率得到methyl O-(3-S-acetyl-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