methyl O-(4,6-O-benzylidene-2-O-benzoyl-β-D-gulopyranosyl)-(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 | 1360878-42-7

• 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-β-D-gulopyranosyl)-(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: 1360878-42-7
• 化学式: C₁₁₅H₁₀₇NO₃₁
• 分子量: 1999.1
• InChiKey: UNDFBRCJQFYILQ-JZSNOLASSA-N

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 methyl O-(4,6-O-benzylidene-2-O-benzoyl-β-D-gulopyranosyl)-(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 作用下， 以 二氯甲烷 为溶剂， 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：

  在 四丁基亚硝酸铵 作用下， 以 乙腈 为溶剂， 以250 mg的产率得到methyl O-(4,6-O-benzylidene-2-O-benzoyl-β-D-gulopyranosyl)-(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