methyl 3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside | 135129-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
• CAS: 135129-67-8
• 化学式: C₄₁H₄₀O₁₃
• 分子量: 740.761
• InChiKey: ZVEKAUZXPODRFS-PQHPERJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  54.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  162.35
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl 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 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 methyl α-L-rhamnopyranosyl-(1->3)-α-D-rhamnopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->2)-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：

  methyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 乙酰氯 作用下， 以 甲醇 为溶剂， 以93%的产率得到methyl 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