ethyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimidoyl-1-deoxy-1-thio-β-D-glucopyranoside | 1340473-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimidoyl-1-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3-(1,3-dioxoisoindol-2-yl)-2-ethylsulfanyl-6-(phenylmethoxymethyl)oxan-4-yl] acetate
• CAS: 1340473-48-4
• 化学式: C₅₄H₅₇NO₁₃S
• 分子量: 960.111
• InChiKey: LKACXYZRROYVEE-VVYQVIALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  69
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  180
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  ethyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimidoyl-1-deoxy-1-thio-β-D-glucopyranoside 、 4-methoxyphenyl (2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 perchloric acid adsorbed on silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以77%的产率得到4-methoxyphenyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)-(2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Convergent synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14

  摘要：

  An efficient synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14 is reported. A one-pot, two step iterative glycosylation and [3+2] block synthetic strategy have been adopted for the construction of the pentasaccharide derivative 11, which was then transformed into target compound 1 after a series of functional group transformations. The primary hydroxyl group has been selectively oxidized to a carboxylic acid functionality without affecting the secondary hydroxyl groups. HClO4-SiO2 has been used as a solid acid substitute in all glycosylation and functional group transformations. The yields were excellent in all glycosylation steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.004
• 作为产物：
  描述：

  O-(2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate 、 ethyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 perchloric acid adsorbed on silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到ethyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimidoyl-1-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Convergent synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14

  摘要：

  An efficient synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14 is reported. A one-pot, two step iterative glycosylation and [3+2] block synthetic strategy have been adopted for the construction of the pentasaccharide derivative 11, which was then transformed into target compound 1 after a series of functional group transformations. The primary hydroxyl group has been selectively oxidized to a carboxylic acid functionality without affecting the secondary hydroxyl groups. HClO4-SiO2 has been used as a solid acid substitute in all glycosylation and functional group transformations. The yields were excellent in all glycosylation steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.004