2-azidoethyl (3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1554556-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl (3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS: 1554556-56-7
• 化学式: C₄₉H₅₃N₃O₁₁
• 分子量: 859.973
• InChiKey: RSEBDXDBZMXMCG-KYPDEDSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  63.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  161.29
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-azidoethyl (3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 、 ethyl (2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以69%的产率得到2-azidoethyl (2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1→3)-(4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Convergent synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O44

  摘要：

  A convergent synthetic strategy has been developed for the synthesis of a pentasaccharide fragment corresponding to the O-antigen of Salmonella enterica 044 strain. An intermediate tetrasaccharide derivative was prepared by a [2+2] block glycosylation of two disaccharide derivatives. The p-methoxybenzyl (PMB) group has been used as the in situ temporary protecting group minimizing the number of functional group manipulation steps. The application of the armed-disarmed glycosylation concept reduced the number of steps in the synthetic strategy. The glycosylation steps were highly stereoselective and high yielding. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.005
• 作为产物：
  描述：

  、 2-azidoethyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.75h， 以74%的产率得到2-azidoethyl (3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Convergent synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O44

  摘要：

  A convergent synthetic strategy has been developed for the synthesis of a pentasaccharide fragment corresponding to the O-antigen of Salmonella enterica 044 strain. An intermediate tetrasaccharide derivative was prepared by a [2+2] block glycosylation of two disaccharide derivatives. The p-methoxybenzyl (PMB) group has been used as the in situ temporary protecting group minimizing the number of functional group manipulation steps. The application of the armed-disarmed glycosylation concept reduced the number of steps in the synthetic strategy. The glycosylation steps were highly stereoselective and high yielding. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.005