3,4-di-O-benzoyl-1,2-O-octoxyethylidene-β-L-rhamnopyranose | 402913-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-di-O-benzoyl-1,2-O-octoxyethylidene-β-L-rhamnopyranose
• 英文别名: [(3aR,5S,6S,7R,7aR)-7-benzoyloxy-2,5-dimethyl-2-octoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6-yl] benzoate
• CAS: 402913-26-2
• 化学式: C₃₀H₃₈O₈
• 分子量: 526.627
• InChiKey: BKVXXLDJCSJYEM-ZBHZTZARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-1,2-O-octoxyethylidene-β-L-rhamnopyranose 在 三氟甲磺酸三甲基硅酯 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 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
• 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 、 四丁基溴化铵 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 3,4-di-O-benzoyl-1,2-O-octoxyethylidene-β-L-rhamnopyranose
  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.