ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside | 1187766-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• CAS: 1187766-01-3
• 化学式: C₅₂H₅₃NO₁₂S
• 分子量: 916.058
• InChiKey: KDZBYNKGMPVALP-BTDXZDFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  66.0
• 可旋转键数：
  17.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  137.52
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 、 4-methoxyphenyl (2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-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 为溶剂， 反应 1.0h， 以75%的产率得到4-methoxyphenyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->3)-(2-O-benzyl-4,6-obenzylidene-α-D-galactopyranosyl)-(1>4)-(2,3-di-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  First synthesis of a pentasaccharide repeating unit of the O-antigenic polysaccharide from enterohaemorrhagic Escherichia coli O48:H21

  摘要：

  A concise synthesis of a pentasaccharide as its 4-methoxyphenyl glycoside, found in the O-antigenic polysaccharide of enterohaemorrhagic Escherichia coli O48:H21 has been achieved for the first time in excellent yield. Most of the intermediate steps are high yielding and the stereooutcome of each glycosylation step was excellent. Stereoselective glycosylation and removal of the 4-methoxybenzyl group were achieved in one-pot by tuning the reaction conditions. A late-stage TEMPO-mediated oxidation strategy has been adopted for the oxidation of a primary hydroxyl group to carboxylic acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.026
• 作为产物：
  描述：

  ((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-2-yl)methyl acetate 、 ethyl 4,6-O-benzylidene-2-deoxy-2-(N-phthalimido)-1-thio-β-D-galactopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  First synthesis of a pentasaccharide repeating unit of the O-antigenic polysaccharide from enterohaemorrhagic Escherichia coli O48:H21

  摘要：

  A concise synthesis of a pentasaccharide as its 4-methoxyphenyl glycoside, found in the O-antigenic polysaccharide of enterohaemorrhagic Escherichia coli O48:H21 has been achieved for the first time in excellent yield. Most of the intermediate steps are high yielding and the stereooutcome of each glycosylation step was excellent. Stereoselective glycosylation and removal of the 4-methoxybenzyl group were achieved in one-pot by tuning the reaction conditions. A late-stage TEMPO-mediated oxidation strategy has been adopted for the oxidation of a primary hydroxyl group to carboxylic acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.026