2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl fluoride | 147384-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl fluoride
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-fluorooxan-2-yl]methyl benzoate
• CAS: 147384-47-2
• 化学式: C₃₄H₂₇FO₉
• 分子量: 598.581
• InChiKey: OWVCLZCQOHOGFK-IXYVTWBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl fluoride 在 三氟化硼乙醚 、 四丁基氟化铵 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 28.5h， 生成 octyl α-D-mannopyranosyl-(1->6)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases

  摘要：

  Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MIT at 1.4, MIT at 1.2, and MIT at 1.5, respectively. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00215-7
• 作为产物：
  描述：

  2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 在 potassium hydrogen bifluoride 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以81%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases

  摘要：

  Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MIT at 1.4, MIT at 1.2, and MIT at 1.5, respectively. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00215-7

文献信息

• Reactions with and in anhydrous hydrogen fluoride systems. Part 8. Triethylamine trishydrofluoride — a convenient reagent for the stereoselective synthesis of glycosyl fluorides
  作者：Ralf Miethchen、Gundula Kolp

  DOI：10.1016/s0022-1139(00)82194-6

  日期：1993.1

  Stereoselective fluorinations are effected by bromine—fluorine exchange at glycosyl bromides of the D- and L-series using triethylamine trishydrofluoride. Pyranosyl fluorides of D-xylose, L-arabinose, D-glucose, D-mannose and L-rhamnose derivatives, as well as of D-galacturonic acid esters, have been prepared. The influence of neighbouring groups in the 2-position is considered.

  立体选择性氟化是通过使用三乙胺三氢氟化物在D系列和L系列的糖基溴上进行溴-氟交换来实现的。已经制备了D-木糖，L-阿拉伯糖，D-葡萄糖，D-甘露糖和L-鼠李糖衍生物以及D-半乳糖醛酸酯的吡喃磺酰氟。考虑在2位上相邻基团的影响。
• C-5 Epimerisation of d-Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity
  作者：Vito Ferro、Nicholas W. See、Gregory K. Pierens、Elizabeth H. Krenske

  DOI：10.1055/a-2149-4586

  日期：2024.3

  effect has so far been exploited to provide short and efficient synthetic routes to rare l-ido sugars. However, the importance of anomeric configuration to its success has remained experimentally unverified. We now report on the synthesis of α- and β-configured per-O-benzoylated mannopyranosyl fluorides and initially show that their reactivity towards photo-bromination is strongly dependent on the anomeric

  迄今为止，氟导向效应已被用来为稀有化合物提供短而有效的合成路线。我-伊多糖。然而，异头构型对其成功的重要性尚未得到实验验证。我们现在报道了α-和β-构型全O-苯甲酰化吡喃甘露糖基氟化物的合成，并初步表明它们对光溴化的反应性强烈依赖于异头构型。然后，通过揭示分离的 5- C-溴糖的自由基还原观察到的立体选择性的显着差异，验证了氟导向效应的立体化学基础。这项工作重要的是提供了一种供体功能化衍生物的合成路线我-古洛糖并揭示了对糖基自由基行为的新见解。
• Synthesis of octyl S-glycosides of tri- to pentasaccharide fragments related to the GPI anchor of Trypanosoma brucei
  作者：Ralf Dettmann、Thomas Ziegler

  DOI：10.1016/j.carres.2011.08.001

  日期：2011.11

  The three oligosaccharide octyl-S-glycosides Man-alpha 1,6-Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (19), Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (27) and Man-alpha 1,2-Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (37), related to the GPI anchor of Trypanosoma brucei were prepared by a stepwise and block-wise approach from octyl 2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-alpha-D-glucopyranoside (8) and octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-1-thio-alpha-D-mannopyransoside (9). Glucosamine derivative 8 was obtained from 1,3,4,6-tetra-O-acetyl-2-azido-2-desoxy-beta-D-glucopyranose (1) in five steps. Mannoside 9 was converted into the corresponding imidate 12 and coupled with 8 to give disaccharide octyl-S-glycoside 13 which was further mannosylated to afford trisaccharide 19 upon deprotection. Likewise, mannoside 9 was galactosylated, converted into the corresponding imidate and coupled with 8 to give trisaccharide 25. Mannosylation of the latter afforded tetrasaccharide 27 upon deprotection. Condensation of 25 with disaccharide imidate 35 gave, upon deprotection of the intermediates, the corresponding pentasaccharide octyl-S-glycoside 37. Saccharides 19, 27 and 37 are suitable substrates for studying the enzymatic glycosylation pattern of the GPI anchor of T. brucei. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases
  作者：T Ziegler

  DOI：10.1016/s0008-6215(96)00215-7

  日期：1996.12.13

  Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MIT at 1.4, MIT at 1.2, and MIT at 1.5, respectively. (C) 1996 Elsevier Science Ltd.