octyl 3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside | 402913-29-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: Bz(-3)[Bz(-4)]Rha(a1-2)[Bz(-3)][Bz(-4)]Rha(a)-O-octyl；[(2S,3S,4S,5R,6S)-4-benzoyloxy-6-[(2R,3R,4R,5S,6S)-4,5-dibenzoyloxy-6-methyl-2-octoxyoxan-3-yl]oxy-5-hydroxy-2-methyloxan-3-yl] benzoate
• CAS: 402913-29-5
• 化学式: C₄₈H₅₄O₁₃
• 分子量: 838.949
• InChiKey: AZYFECBNQKBRNU-YYZXZFJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl 2,2,2-trichloroacetamidate 、 octyl 3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-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， 反应 2.0h， 以77.9%的产率得到octyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-D-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of an l-rhamnose tetrasaccharide, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci

  摘要：

  A tetrasaccharide, alpha -L-Rhap-(1 -->3)-alpha -L-Rhap-(1 -->2)-alpha -L-Rhap-(1 --> 2)-L-Rhap, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci was synthesized as its methyl and octyl glycosides. Selective 3-O-glycosylation of allyl alpha -L-rhamnopyranoside with 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl trichloroacetimidate gave allyl 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-alpha -L-rhamnopyranoside (3). Benzoylation, deallylation, and trichloroacetimidation afforded 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha -L-rhamnopyranosyl trichloroacetimidate (6). Self condensation of 3,4-di-O-benzoyl-beta -L-rhamnopyranose 1,2-methyl orthoester or 1,2-octyl orthoester gave methyl or octyl 2-O-acetyl-3,4-di-O-benzoyl-alpha -L-rhamnopyranosyl-(1 -->2)-3,4-di-O-benzOyl-alpha -L-rhamnopyranoside (16 or 17), and subsequent selective deacetylation gave the disaccharide acceptor (18 or 19). Coupling of 6 with 18 (or 19), followed by deacylation in ammonia-saturated methanol, produced the target tetrasacharide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00258-0
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-甘露糖基溴化物 在 吡啶 、 2,4-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基溴化铵 、 sodium methylate 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 octyl 3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of an l-rhamnose tetrasaccharide, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci

  摘要：

  A tetrasaccharide, alpha -L-Rhap-(1 -->3)-alpha -L-Rhap-(1 -->2)-alpha -L-Rhap-(1 --> 2)-L-Rhap, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci was synthesized as its methyl and octyl glycosides. Selective 3-O-glycosylation of allyl alpha -L-rhamnopyranoside with 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl trichloroacetimidate gave allyl 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-alpha -L-rhamnopyranoside (3). Benzoylation, deallylation, and trichloroacetimidation afforded 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha -L-rhamnopyranosyl trichloroacetimidate (6). Self condensation of 3,4-di-O-benzoyl-beta -L-rhamnopyranose 1,2-methyl orthoester or 1,2-octyl orthoester gave methyl or octyl 2-O-acetyl-3,4-di-O-benzoyl-alpha -L-rhamnopyranosyl-(1 -->2)-3,4-di-O-benzOyl-alpha -L-rhamnopyranoside (16 or 17), and subsequent selective deacetylation gave the disaccharide acceptor (18 or 19). Coupling of 6 with 18 (or 19), followed by deacylation in ammonia-saturated methanol, produced the target tetrasacharide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00258-0

文献信息

• Synthesis of an l-rhamnose tetrasaccharide, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci
  作者：Jianjun Zhang、Yuliang Zhu、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00258-0

  日期：2001.11

  A tetrasaccharide, alpha -L-Rhap-(1 -->3)-alpha -L-Rhap-(1 -->2)-alpha -L-Rhap-(1 --> 2)-L-Rhap, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci was synthesized as its methyl and octyl glycosides. Selective 3-O-glycosylation of allyl alpha -L-rhamnopyranoside with 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl trichloroacetimidate gave allyl 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-alpha -L-rhamnopyranoside (3). Benzoylation, deallylation, and trichloroacetimidation afforded 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha -L-rhamnopyranosyl trichloroacetimidate (6). Self condensation of 3,4-di-O-benzoyl-beta -L-rhamnopyranose 1,2-methyl orthoester or 1,2-octyl orthoester gave methyl or octyl 2-O-acetyl-3,4-di-O-benzoyl-alpha -L-rhamnopyranosyl-(1 -->2)-3,4-di-O-benzOyl-alpha -L-rhamnopyranoside (16 or 17), and subsequent selective deacetylation gave the disaccharide acceptor (18 or 19). Coupling of 6 with 18 (or 19), followed by deacylation in ammonia-saturated methanol, produced the target tetrasacharide. (C) 2001 Elsevier Science Ltd. All rights reserved.