2,3,4-tri-O-acetyl-α-D-rhamnopyranosyl bromide | 14227-85-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-α-D-rhamnopyranosyl bromide
• 英文别名: 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide；α-acetobromorhamnose；Tri-O-acetyl-α-D-rhamnopyranosylbromid；[(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-bromo-2-methyloxan-3-yl] acetate
• CAS: 14227-85-1
• 化学式: C₁₂H₁₇BrO₇
• 分子量: 353.167
• InChiKey: XUZQAPSYNYIKSR-SZRPSHQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-D-rhamnopyranosyl bromide 在 potassium disulphite 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 cinnamyl 6-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Inhibition of delayed hypersensitivity reactions by cinnamyl 1-thioglycosides

  摘要：

  Cinnamyl 1-thio-alpha-D-manno(and L-rhamno)pyranosides have good inhibitory effects in an antigen-specific T cell proliferation assay. The beta anomers are slightly less effective than the alpha anomers. The 6-substituted analogues of cinnamyl 1-thio-alpha-D-mannopyranoside such as 6-deoxy and 6-O-methyl derivatives also block macrophages in presenting the antigen to T cells. D-Mannose and L-rhamnose, when tested by themselves with no modifications, did not block at concentrations up to 1 mM. These cinnamyl 1-thioglycosides when given ip or po at 3-30 mg/kg to mice significantly inhibited the delayed type hypersensitivity reaction as measured by footpad swelling.

  DOI：

  10.1021/jm00387a021
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-mannopyranose 在 氢溴酸 、 溶剂黄146 作用下， 反应 2.0h， 生成 2,3,4-tri-O-acetyl-α-D-rhamnopyranosyl bromide
  参考文献：
  名称：

  P 1-（11-苯氧基十一烷基）-P 2-（2-乙酰氨基-2-脱氧-3-O-α-D-鼠李糖吡喃糖基-α-D-吡喃葡萄糖基）二磷酸酯和P 1-（11-苯氧基十一烷基）-的合成P 2-（2-乙酰氨基-2-脱氧-3-O-β-D-吡喃半乳糖基-α-D-吡喃半乳糖基）二磷酸用于铜绿假单胞菌和大肠杆菌O104中O抗原多糖的生物合成研究

  摘要：

  首次合成了两个新的苯氧基十一烷基二磷酸糖：P1-（11-苯氧基十一烷基）-P2-（2-乙酰氨基-2-脱氧-3-O-α-D-鼠李糖基吡喃糖基-α-D-葡萄糖基吡喃糖基）二磷酸和P1 -（11-苯氧基十一烷基）-P2-（2-乙酰氨基-2-脱氧-3-O-β-D-吡喃并吡喃糖基-α-D-吡喃并吡喃糖基）二磷酸酯，以研究O抗原重复单元的生物合成的第三步铜绿假单胞菌和大肠杆菌O104中的多糖分别。

  DOI：

  10.1016/j.carres.2017.10.016

文献信息

• Electrochemical formation of glycals in THF
  作者：J.D Parrish、R.Daniel Little

  DOI：10.1016/s0040-4039(01)01544-1

  日期：2001.10

  existing electrochemical approaches to these types of species and is amenable to scale up for large-scale production. In addition, this work is intended to provide a means of employing electrochemistry that can be duplicated in most organic chemistry laboratories using readily available glassware and equipment.

  提出了一种从糖基溴化物生产不饱和糖的新方法。这项工作简化了对这些类型物质的现有电化学方法，并可以扩大规模以进行大规模生产。此外，这项工作旨在提供一种使用电化学的方法，可以使用现成的玻璃器皿和设备在大多数有机化学实验室中复制这种方法。
• Synthesis and conformational analysis of methyl 3-O-[α-l(and d)-rhamnopyranosyl]maltoside derivatives: A branched trisaccharide with the central glucopyranose residue in the 1C4 conformation
  作者：Klaus Bock、José Fernandez-Bolaños Guzman、Rolf Norrestam

  DOI：10.1016/0008-6215(88)84113-2

  日期：1988.8

  fluorides (24 and 25), and the latter transformed into the 1,6-anhydro derivatives by treatment with strong base. The conformations of the acetylated derivatives have been analysed by 1H- and 13C-n.m.r. spectroscopy. In most of the branched trisaccharide derivatives, the conformation of the central glucopyranose residue is predominantly 1C4. X-Ray analysis showed that, in the solid state for the glycosyl

  摘要支链三糖4-O-α-d-吡喃葡糖基-3-O-α-l-鼠李糖吡喃糖基-β-d-吡喃葡糖是模型，它来自于志贺氏志贺菌血清型I，1a，具有以下结构： →2）-α-l-Rha-（1→3）-α-l-活性，使用三氟甲磺酸银促进的糖基化反应。类似地，已经合成了模型二糖葡糖苷甲基3-O-α-1（和d）-鼠李吡喃糖基-α（和β）-d-葡糖吡喃糖苷。三糖的乙酰化衍生物已转化为它们的糖基溴化物（22和23）和糖基氟化物（24和25），并且通过用强碱处理将后者转化为1,6-脱水衍生物。乙酰化衍生物的构象已通过1H-和13C-nmr光谱分析。在大多数支链三糖衍生物中，中央吡喃葡萄糖残基的构象主要是1C4。X射线分析表明，在糖基氟化物24的固态下，中心吡喃葡萄糖残基的构象是1C4。
• Synthesis of the Trisaccharide Repeating Unit of the Atypical <i>O</i>-Antigen Polysaccharide from Danish <i>Helicobacter p</i><i>ylori</i> Strains Employing the 2‘-Carboxybenzyl Glycoside
  作者：Yong Tae Kwon、Yong Joo Lee、Kyunghoon Lee、Kwan Soo Kim

  DOI：10.1021/ol048648u

  日期：2004.10.1

  [reaction: see text] Synthesis of the unique trisaccharide repeating unit of the O-polysaccharide of the lipopolysaccharide from Danish Helicobacter pylori strains has been accomplished. Key steps include the coupling of three monosaccharide moieties by glycosylations employing the 2'-carboxybenzyl glycoside method. Also presented is a method for the synthesis of the novel branched sugar, 3-C-methyl-D-mannose

  [反应：见正文]已经从丹麦幽门螺杆菌菌株中合成了脂多糖的O-多糖的独特的三糖重复单元。关键步骤包括使用2'-羧基苄基糖苷方法通过糖基化作用偶联三个单糖部分。还提出了一种新颖的支链糖3-C-甲基-D-甘露糖的合成方法，所述支链糖是三种单糖组分之一。
• Baumann, Herbert; Jansson, Per-Erik; Kenne, Lennart, Journal of the Chemical Society. Perkin transactions I, 1988, p. 209 - 218
  作者：Baumann, Herbert、Jansson, Per-Erik、Kenne, Lennart

  DOI：——

  日期：——
• Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor
  作者：Hasnah Osman、David S. Larsen、Jim Simpson

  DOI：10.1016/j.tet.2009.03.092

  日期：2009.5

  1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-D-arabinopyranose (11) was synthesised from thiophenyl alpha-D-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-alpha-D-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and Subsequent protecting group manipulation gave D-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected D-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.