ethyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-N-phthalimido-1-thio-β-D-galactopyranoside | 1453085-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-N-phthalimido-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-ethylsulfanyl-3-[(2S,3R,4R,5S,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1453085-88-5
• 化学式: C₅₂H₅₃NO₁₂S
• 分子量: 916.058
• InChiKey: GGAFHVNINDZNPK-ZCDUGXNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  66
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  171
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl (2,6-di-O-benzyl-α-D-galactopyranosyl)-(1→6)-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1→3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-N-phthalimido-β-D-galactopyranoside 、 ethyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-N-phthalimido-1-thio-β-D-galactopyranoside 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 1.25h， 以74%的产率得到p-methoxyphenyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(3-O-acetyl-6-O-benzoyl-2-deoxy-2-N-phthalimido-β-D-galactopyranosyl)-(1→3)-(2,6-di-O-benzyl-α-D-galactopyranosyl)-(1→6)-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1→3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-N-phthalimido-β-D-galactopyranoside
  参考文献：
  名称：

  Concise synthesis of a pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O102

  摘要：

  An efficient synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit of the O-antigen of Escherichia coli O102 strain. The target pentasaccharide 1 has been synthesized using a [2+3] block glycosylation strategy. All glycosylation steps are highly stereoselective and high yielding. Concept of armed-disarmed and orthogonal glycosylation strategies has been applied during the synthesis. The target compound has been synthesized using the minimum number of steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.005
• 作为产物：
  描述：

  ethyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-galactopyranoside 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.75h， 生成 ethyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-N-phthalimido-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Concise synthesis of a pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O102

  摘要：

  An efficient synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit of the O-antigen of Escherichia coli O102 strain. The target pentasaccharide 1 has been synthesized using a [2+3] block glycosylation strategy. All glycosylation steps are highly stereoselective and high yielding. Concept of armed-disarmed and orthogonal glycosylation strategies has been applied during the synthesis. The target compound has been synthesized using the minimum number of steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.005