benzyl 4-O-benzoyl-α-L-rhamnopyranoside | 502423-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-4,5-dihydroxy-2-methyl-6-phenylmethoxyoxan-3-yl] benzoate
• CAS: 502423-54-3
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: QAWIHXLHQXCRJN-GELNYDQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 4-O-benzoyl-α-L-rhamnopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 硫脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 22.17h， 生成 benzyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-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
• 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， 反应 2.75h， 生成 benzyl 4-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

• Regioselective Benzoylation of Glycopyranosides by Benzoyl Chloride in the Presence of MoO₂(acac)₂
  作者：E. V. Evtushenko

  DOI：10.1080/07328303.2010.549258

  日期：2010.11.1

  Benzoylation of methyl and benzyl glycopyranosides by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst resulted in 3-benzoates with good yield and high regioselectivity. Simple synthesis of the monobenzoates of some glycopyranosides is suggested.
• 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
• 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.
• Oligomerization of a rhamnanic trisaccharide repeating unit of O-chain polysaccharides from phytopathogenic bacteria
  作者：Emiliano Bedini、Michelangelo Parrilli、Carlo Unverzagt

  DOI：10.1016/s0040-4039(02)02237-2

  日期：2002.12

  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.