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 | 1225196-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 1225196-82-6
• 化学式: C₇₁H₇₀ClNO₁₇S
• 分子量: 1276.85
• InChiKey: AGQKIWWHVOKMPA-NWTALOEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.44
• 重原子数：
  91.0
• 可旋转键数：
  25.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  191.51
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 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 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到methyl 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-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of new sulfonic acid-containing oligosaccharide mimetics of sialyl Lewis A

  摘要：

  Two trisaccharides as new sulfonic acid mimetics of the sialyl Lewis A tetrasaccharide were synthesized. The natural sialic acid residue is replaced by a C-sulfonic acid moiety attached to position C-3' of the lactosamine unit of the mimetics. The L-fucose unit was also replaced by a D-arabinose ring in one of the analogues. Formation of the sulfonic acid moiety on the trisaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the galactose skeleton and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be achieved by double nucleophilic substitution; efficient formation of the gulo-triflate derivatives required low-power microwave activation. Oxidation of the acetylthio group was carried out using Oxone in acetic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.100
• 作为产物：
  描述：

  ethyl 6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-β-D-arabinopyranosyl)-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 、 苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到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
  参考文献：
  名称：

  Synthesis of new sulfonic acid-containing oligosaccharide mimetics of sialyl Lewis A

  摘要：

  Two trisaccharides as new sulfonic acid mimetics of the sialyl Lewis A tetrasaccharide were synthesized. The natural sialic acid residue is replaced by a C-sulfonic acid moiety attached to position C-3' of the lactosamine unit of the mimetics. The L-fucose unit was also replaced by a D-arabinose ring in one of the analogues. Formation of the sulfonic acid moiety on the trisaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the galactose skeleton and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be achieved by double nucleophilic substitution; efficient formation of the gulo-triflate derivatives required low-power microwave activation. Oxidation of the acetylthio group was carried out using Oxone in acetic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.100

文献信息

• Synthesis of a sulfonic acid mimetic of the sulfated Lewis A pentasaccharide
  作者：Zsolt Jakab、Anikó Fekete、Magdolna Csávás、Anikó Borbás、András Lipták、Sándor Antus

  DOI：10.1016/j.carres.2011.12.015

  日期：2012.3

  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.