3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate | 1096154-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
• 英文别名: [(2S,3S,4R,5R,6S)-5-benzoyloxy-2-methyl-4-prop-2-enoxycarbonyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 1096154-19-6
• 化学式: C₂₆H₂₄Cl₃NO₉
• 分子量: 600.837
• InChiKey: COFMKERDOKXGKW-KVIDMWFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 、 p-methoxylphenyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到p-methoxyphenyl 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Two Tetrasaccharides Related to the O-Antigen fromAzospirillum brasilenseS17 andAzospirillum lipoferumSR65

  摘要：

  Synthesis of two isomeric tetrasaccharides, -D-Glup-(12)--L-Rhap-(13)--L- Rhap-(12)--L-Rhap (I) and -D-Glup-(13)--L-Rhap-(13)--L-Rhap-(13)--L-Rhap (II), the repeating units from the lipopolysaccharides of the nitrogen-fixing bacterium Azospirillum brasilense S17 and Azospirillum lipoferum SR65, was achieved via assembly of the building blocks 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl trichloroacetimidate (2), p-methoxyphenyl 3,4-di-O-benzoyl--L-rhamnopyranoside (3), 3-O-allyloxycarbonyl-2,4-di-O-benzoyl--L-rhamnopyranosyl trichloroacetimidate (6), 2,3,4,6-tetra-O-benzoyl--D-glucopyranosyl trichloroacetimidate (8), and p-methoxy phenyl 2,4-di-O-benzoyl--L-rhamnopyranoside (14). Condensation of 3 with 6 or 8 provided the disaccharides 9 or 11, respectively. Deallyloxycarbonylation of 11 gave the disaccharide aceptor 12, while removal of the p-methoxyphenyl group in 9 followed by trichloroacetimidation of the anomeric hydroxyl group afforded the disaccharide donor 10. Meanwhile, disaccharide donor 16 and acceptor 18 were prepared from 6, 8, and 14 similarly. Finally, condensation of 10 with 12 or 16 with 18, followed by deprotection, gave the target tetrasaccharides I or II, respectively.

  DOI：

  10.1080/07328301003786789
• 作为产物：
  描述：

  4-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside 在 吡啶 、 ammonium cerium (IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.33h， 生成 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of Two Tetrasaccharides Related to the O-Antigen fromAzospirillum brasilenseS17 andAzospirillum lipoferumSR65

  摘要：

  Synthesis of two isomeric tetrasaccharides, -D-Glup-(12)--L-Rhap-(13)--L- Rhap-(12)--L-Rhap (I) and -D-Glup-(13)--L-Rhap-(13)--L-Rhap-(13)--L-Rhap (II), the repeating units from the lipopolysaccharides of the nitrogen-fixing bacterium Azospirillum brasilense S17 and Azospirillum lipoferum SR65, was achieved via assembly of the building blocks 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl trichloroacetimidate (2), p-methoxyphenyl 3,4-di-O-benzoyl--L-rhamnopyranoside (3), 3-O-allyloxycarbonyl-2,4-di-O-benzoyl--L-rhamnopyranosyl trichloroacetimidate (6), 2,3,4,6-tetra-O-benzoyl--D-glucopyranosyl trichloroacetimidate (8), and p-methoxy phenyl 2,4-di-O-benzoyl--L-rhamnopyranoside (14). Condensation of 3 with 6 or 8 provided the disaccharides 9 or 11, respectively. Deallyloxycarbonylation of 11 gave the disaccharide aceptor 12, while removal of the p-methoxyphenyl group in 9 followed by trichloroacetimidation of the anomeric hydroxyl group afforded the disaccharide donor 10. Meanwhile, disaccharide donor 16 and acceptor 18 were prepared from 6, 8, and 14 similarly. Finally, condensation of 10 with 12 or 16 with 18, followed by deprotection, gave the target tetrasaccharides I or II, respectively.

  DOI：

  10.1080/07328301003786789

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.
• Synthesis of Two Tetrasaccharides Related to the O-Antigen from<i>Azospirillum brasilense</i>S17 and<i>Azospirillum lipoferum</i>SR65
  作者：Hanqing Zhao、Huiqi Jia、Hongxia Duan、Jianjun Zhang、Daoquan Wang、Xiaomei Liang

  DOI：10.1080/07328301003786789

  日期：2010.4

  Synthesis of two isomeric tetrasaccharides, -D-Glup-(12)--L-Rhap-(13)--L- Rhap-(12)--L-Rhap (I) and -D-Glup-(13)--L-Rhap-(13)--L-Rhap-(13)--L-Rhap (II), the repeating units from the lipopolysaccharides of the nitrogen-fixing bacterium Azospirillum brasilense S17 and Azospirillum lipoferum SR65, was achieved via assembly of the building blocks 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl trichloroacetimidate (2), p-methoxyphenyl 3,4-di-O-benzoyl--L-rhamnopyranoside (3), 3-O-allyloxycarbonyl-2,4-di-O-benzoyl--L-rhamnopyranosyl trichloroacetimidate (6), 2,3,4,6-tetra-O-benzoyl--D-glucopyranosyl trichloroacetimidate (8), and p-methoxy phenyl 2,4-di-O-benzoyl--L-rhamnopyranoside (14). Condensation of 3 with 6 or 8 provided the disaccharides 9 or 11, respectively. Deallyloxycarbonylation of 11 gave the disaccharide aceptor 12, while removal of the p-methoxyphenyl group in 9 followed by trichloroacetimidation of the anomeric hydroxyl group afforded the disaccharide donor 10. Meanwhile, disaccharide donor 16 and acceptor 18 were prepared from 6, 8, and 14 similarly. Finally, condensation of 10 with 12 or 16 with 18, followed by deprotection, gave the target tetrasaccharides I or II, respectively.