1,2-di-O-acetyl-3,4-di-O-benzyl-β-L-rhamnopyranose | 73983-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-di-O-acetyl-3,4-di-O-benzyl-β-L-rhamnopyranose
• CAS: 73983-20-7
• 化学式: C₂₄H₂₈O₇
• 分子量: 428.482
• InChiKey: AZCRUMLPMBQUBQ-NORIUAQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 在 2,6-二甲基吡啶 、 四丁基溴化铵 、 溶剂黄146 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 19.92h， 生成 1,2-di-O-acetyl-3,4-di-O-benzyl-β-L-rhamnopyranose
  参考文献：
  名称：

  Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach

  摘要：

  To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranoside (27) and hexasaccharide propyl alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranoside (33) were synthesized. These oligosaccharides represent the repeating monomer and dimer of the O-antigen, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.005

文献信息

• C-Glycoside D-galacturonates suitable as glycosyl acceptors for the synthesis of allyl C-homo- and rhamno-galacturonan modules
  作者：Mahmoud Farouk、Dirk Michalik、Alexander Villinger、Christian Vogel

  DOI：10.3998/ark.5550190.0014.226

  日期：——

  -2-enyl)-α-D- galactopyranuronate were synthesized in 53% and 44% yields respectively and with moderate stereoselectivity. The synthesis of 1,2- O-acetyl-3,4-di-O-benzyl-L-rhamnopyranose (α/β) and 2- O-acetyl-1-bromo-3,4-di-O-benzyl-α-L-rhamnopyranosyl suitable as glycosyl donors is described. The disaccharide methyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1 →4) - 2,3-di-O-benzyl-1-deoxy

  甲基 2,3-di-O-benzyl-1-deoxy-1-(prop-2-enyl)-α-D-galactopyranuronate 和 benzyl 2,3-di-O-benzyl-1-deoxy-1-(prop -2-烯基)-α-D-吡喃半乳糖醛酸制备为糖基受体。糖基供体苄基 4-O-乙酰基-2,3-二-O-苄基-1-(三氯乙酰亚氨酰氧基)-α-D-吡喃半乳糖醛酸和苄基 4-O-乙酰基-2,3-二-O-苄基-1 -(三氯乙酰亚氨基酰氧基)-β-D-吡喃半乳糖基糖醛酸酯分别以98%和76%的产率合成。二糖甲基（甲基 4-O-乙酰基-2,3-二-O-苄基-α/β-D-吡喃半乳糖醛酸）-(1 →4)-2,3-二-O-苄基-1-脱氧-1 -(prop-2-enyl)-α-D-吡喃半乳糖和苄基(benzyl 4-O-acetyl-2,3-di-O-benzyl-α/β-D-galactopyranosyluronate)-(1
• Carbon-13 n.m.r.-spectral study of l-rhamnose acetates
  作者：Vince Pozsgay、András Neszmélyi

  DOI：10.1016/s0008-6215(00)85326-4

  日期：——