4-methoxyphenyl 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-6-deoxy-L-talopyranoside | 1096154-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-6-deoxy-L-talopyranoside
• CAS: 1096154-20-9
• 化学式: C₅₁H₄₈O₁₆
• 分子量: 916.933
• InChiKey: YGUAGBCEALPAHG-FWHPMWBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  67.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  186.88
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-6-deoxy-L-talopyranoside 在 四(三苯基膦)钯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到4-methoxyphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-6-deoxy-L-talopyranoside
  参考文献：
  名称：

  Synthesis of the 6-deoxytalose-containing tetrasaccharide of the glycopeptidolipid from Mycobacterium intracellare serotype 7

  摘要：

  An efficient synthesis of 4-methoxyphenyl alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-6-deoxy-alpha-L-Talp, the tetrasaccharide related to the GPLs of Mycobacterium intracellare serotype 7, was achieved with 4-methoxyphenyl 3,4-di-O-benzoyl-6-deoxy-alpha-L-talopyranoside (6c) as the key intermediate which was obtained through selective 3-O-benzoylation of 4-O-benzoyl-6-deoxy-alpha-L-taloside. Coupling of 6c with 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate followed by removal of the allyloxycarbonyl protecting group afforded the disaccharide acceptor 11. Condensation of 11 with 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate and subsequent deprotection gave the target tetrasaccharide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.010
• 作为产物：
  描述：

  4-methoxyphenyl 3,4-di-O-benzoyl-6-deoxy-α-L-talopyranoside 、 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到4-methoxyphenyl 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-6-deoxy-L-talopyranoside
  参考文献：
  名称：

  Synthesis of the 6-deoxytalose-containing tetrasaccharide of the glycopeptidolipid from Mycobacterium intracellare serotype 7

  摘要：

  An efficient synthesis of 4-methoxyphenyl alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-6-deoxy-alpha-L-Talp, the tetrasaccharide related to the GPLs of Mycobacterium intracellare serotype 7, was achieved with 4-methoxyphenyl 3,4-di-O-benzoyl-6-deoxy-alpha-L-talopyranoside (6c) as the key intermediate which was obtained through selective 3-O-benzoylation of 4-O-benzoyl-6-deoxy-alpha-L-taloside. Coupling of 6c with 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate followed by removal of the allyloxycarbonyl protecting group afforded the disaccharide acceptor 11. Condensation of 11 with 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate and subsequent deprotection gave the target tetrasaccharide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.010