4-methoxyphenyl L-rhamnopyranosyl-(1->3)-L-rhamnopyranosyl-(1->3)-L-rhamnopyranosyl-(1->2)-6-deoxy-L-talopyranoside | 1096154-34-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl L-rhamnopyranosyl-(1->3)-L-rhamnopyranosyl-(1->3)-L-rhamnopyranosyl-(1->2)-6-deoxy-L-talopyranoside
• 英文别名: Rha(a1-3)Rha(a1-3)Rha(a1-2)6-deoxy-L-Tal(a)-O-Ph(4-OMe)；(2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5S,6S)-4,5-dihydroxy-2-(4-methoxyphenoxy)-6-methyloxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1096154-34-5
• 化学式: C₃₁H₄₈O₁₈
• 分子量: 708.711
• InChiKey: JAOMQPMPKMLBPG-TVCCCQJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  265
• 氢给体数：
  9
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  4-methoxyphenyl 2,3,4-tri-O-benzoyl-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-6-deoxy-L-talopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以91%的产率得到4-methoxyphenyl L-rhamnopyranosyl-(1->3)-L-rhamnopyranosyl-(1->3)-L-rhamnopyranosyl-(1->2)-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

文献信息

• Synthesis of the 6-deoxytalose-containing tetrasaccharide of the glycopeptidolipid from Mycobacterium intracellare serotype 7
  作者：Shiqiang Yan、Xiaomei Liang、Peiyu Diao、Ye. Yang、Jianjun Zhang、Daoquan Wang、Fanzuo Kong

  DOI：10.1016/j.carres.2008.09.010

  日期：2008.12

  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.