benzyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside | 89756-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: benzyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside；[(2S,3S,4S,5R,6R)-4-benzoyloxy-5-hydroxy-2-methyl-6-phenylmethoxyoxan-3-yl] benzoate
• CAS: 89756-10-5
• 化学式: C₂₇H₂₆O₇
• 分子量: 462.499
• InChiKey: QFJZFLKHUWJBRB-VIGIAUSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 sodium methylate 、 三氟甲烷磺酸甲酯 作用下， 以 乙醚 为溶剂， 反应 18.0h， 生成 2-O-β-L-fucopyranosyl-β-L-rhamnopyranose
  参考文献：
  名称：

  Jansson, Per-Erik; Kenne, Lennart; Persson, Kerstin, Journal of the Chemical Society. Perkin transactions I, 1990, p. 591 - 598

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl α-L-rhamnopyranoside 在 吡啶 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.42h， 生成 benzyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Oligomerization of a rhamnanic trisaccharide repeating unit of O-chain polysaccharides from phytopathogenic bacteria

  摘要：

  An efficient synthesis of a protected trisaccharide building block alpha-L-Rha(1-->3)-alpha-L-Rha(1-->2)-alpha-L-Rha related to the structure of many lipopolysaccharide 0-chains from phytopathogenic bacteria has been developed. The protecting group pattern consisting of benzoyl, benzyl and chloroacetyl groups facilitated the use of the trisaccharide building block in the synthesis of two higher oligomers, an oligorhamnosyl hexasaccharide and a nonasaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02237-2

文献信息

• 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
  作者：N. �. Bairamova、L. V. Bakinovskii、N. K. Kochetkov

  DOI：10.1007/bf01142795

  日期：1985.5
• 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 disaccharide analogues of methyl 4-O-α-d-galactopyranosyl-β-d-galactopyranoside (“methyl urobioside”), the minimum structure recognised by p-fimbriated E. coli
  作者：Thomas Norberg、Stefan Oscarson、Szönyi Maria

  DOI：10.1016/s0008-6215(00)90311-2

  日期：1986.9
• JANSSON, PER-ERIK;KENNE, LENNART;PERSSON, KERSTIN;WIDMALM, GORAN, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 591-598
  作者：JANSSON, PER-ERIK、KENNE, LENNART、PERSSON, KERSTIN、WIDMALM, GORAN

  DOI：——

  日期：——
• Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010
  作者：Emiliano Bedini、Gaspare Barone、Carlo Unverzagt、Michelangelo Parrilli

  DOI：10.1016/j.carres.2003.10.002

  日期：2004.1

  The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit. (C) 2003 Elsevier Ltd. All rights reserved.