ethyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 1225196-75-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-2-ethylsulfanyl-5-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1225196-75-7
• 化学式: C₆₄H₇₁NO₁₉S
• 分子量: 1190.33
• InChiKey: IDQYDCXOZYQWST-SXFJBVRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  85
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  251
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到ethyl 6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-3-O-(β-D-galactopyranosyl)-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
• 作为产物：
  描述：

  perbenzyl fucosyl bromide 、 ethyl 6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 26.0h， 以56%的产率得到ethyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-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