methyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside | 89756-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: methyl-2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside
• CAS: 89756-06-9
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: AIYCKOUVNBUIRP-CDZNBZLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 盐酸 作用下， 反应 16.0h， 以90%的产率得到methyl 3,4-di-O-benzoyl α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the principal chain of the 0-antigenic polysaccharides ofShigella flexneri Communication 1. Synthesis of 2,4- and 3,4-di-o-benzoyl-?-L-rhamnopyranosides by a combination of selective acylation and deacetylation, and the synthesis of 1,2-di-o-acetyl-3,4-di-o-benzoyl-L-rhamnopyranose via 1,2-o-benzylidene-3,4-di-o-benzoyl-?-L-rhamnopyranose

  摘要：

  DOI：

  10.1007/bf01142795
• 作为产物：
  描述：

  3,4-di-O-benzoyl-1,2-O-methoxyethylidene-β-L-rhamnopyranose 在 mercury dibromide 作用下， 以 硝基甲烷 为溶剂， 以90%的产率得到methyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the principal chain of the 0-antigenic polysaccharides ofShigella flexneri Communication 1. Synthesis of 2,4- and 3,4-di-o-benzoyl-?-L-rhamnopyranosides by a combination of selective acylation and deacetylation, and the synthesis of 1,2-di-o-acetyl-3,4-di-o-benzoyl-L-rhamnopyranose via 1,2-o-benzylidene-3,4-di-o-benzoyl-?-L-rhamnopyranose

  摘要：

  DOI：

  10.1007/bf01142795

文献信息

• Synthesis of specifically deoxygenated disaccharide derivatives of the Shigella dysenteriae type 1 O-antigen
  作者：Laurence A. Mulard、Cornelis P.J. Claudemans

  DOI：10.1016/0008-6215(95)00122-a

  日期：1995.9

  The synthesis of methyl O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-D-galactopyranosides specifically deoxygenated at position 2 (31), or 4 (21) of the rhamnopyranosyl residue was accomplished using methyl 3,4,6-tri-O-benzoyl-alpha-D-galactopyranoside (18) as the glycosyl acceptor. Phenyl thionocarbonate activation of the penta-O-benzoylated disaccharide precursor followed by Barton reduction and Zemplén

  使用3,4甲基合成在鼠李糖吡喃糖基残基的位置2（31）或4（21）上特别脱氧的甲基O-α-L-鼠李糖吡喃糖基-（1→2）-α-D-吡喃半乳糖苷，6-三-O-苯甲酰基-α-D-吡喃半乳糖苷（18）作为糖基受体。五-O-苯甲酰化二糖前体的苯硫代碳酸酯活化，然后进行Barton还原和Zemplén酯交换，得到31，而通过脱氧单糖供体与18的缩合反应以及随后产物的脱苯甲酰化，得到21。
• Selective removal of O-acetyl groups in the presence of O-benzoyl groups by acid-catalysed methanolysis
  作者：Narguiz É. Byramova、Michael V. Ovchinnikov、Leon V. Backinowsky、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(83)88370-0

  日期：1983.12
• 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.