2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol | 544686-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol
• 英文别名: 1-O-tert-butyldiphenylsilyl-2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-sn-glycerol；N-[(2S,3R,4R,5S,6R)-2-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxypropan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 544686-91-1
• 化学式: C₄₈H₅₇NO₈Si
• 分子量: 804.068
• InChiKey: SXLJFRCMDGJXRD-DARATDDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
  参考文献：
  名称：

  Fluorous Linker Facilitated Synthesis of Teichoic Acid Fragments

  摘要：

  The use of perfluorooctylpropylsulfonylethanol as a new phosphate protecting group and fluorous linker is evaluated in the stepwise solution phase synthesis of a number of biologically relevant (carbohydrate substituted) glycerol teichoic acid fragments. Teichoic acid fragments, up to the dodecamer level, were assembled by means of phosphoramidite chemistry, using a relatively small excess of the building blocks and a repetitive efficient purification procedure of the protected intermediates by fluorous solid phase extraction (F-SPE).

  DOI：

  10.1021/ol2033652
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate 在 吡啶 、 1,3-丙二硫醇 、 Wilkinson's catalyst 、 三氟甲磺酸三甲基硅酯 、 水 、 sodium methylate 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol
  参考文献：
  名称：

  合成第一个完全活性的脂磷壁酸。

  摘要：

  DOI：

  10.1002/anie.200390243

文献信息

• Synthesis of structural variants of Staphylococcus aureus lipoteichoic acid (LTA)
  作者：Ignacio Figueroa-Perez、Andreas Stadelmaier、Siegfried Morath、Thomas Hartung、Richard R. Schmidt

  DOI：10.1016/j.tetasy.2004.11.070

  日期：2005.1

  Based on 1,2-O-isopropylidene-sn-glyerol, which is readily available from D-mannitol, five chiral building blocks for the construction of structural variants of Staphylococcus aureus LTA designed and synthesized. Ligation of these building blocks led readily to the target molecules 1 and 2. They demonstrated that the D-alanine residues at the glycerophosphate backbone are decisive for the activation of the immune system. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of the First Fully Active Lipoteichoic Acid
  作者：Andreas Stadelmaier、Siegfried Morath、Thomas Hartung、Richard R. Schmidt

  DOI：10.1002/anie.200390243

  日期：2003.2.24
• Fluorous Linker Facilitated Synthesis of Teichoic Acid Fragments
  作者：Wouter F. J. Hogendorf、Lucien N. Lameijer、Thomas J. M. Beenakker、Herman S. Overkleeft、Dmitri V. Filippov、Jeroen D. C. Codée、Gijsbert A. Van der Marel

  DOI：10.1021/ol2033652

  日期：2012.2.3

  The use of perfluorooctylpropylsulfonylethanol as a new phosphate protecting group and fluorous linker is evaluated in the stepwise solution phase synthesis of a number of biologically relevant (carbohydrate substituted) glycerol teichoic acid fragments. Teichoic acid fragments, up to the dodecamer level, were assembled by means of phosphoramidite chemistry, using a relatively small excess of the building blocks and a repetitive efficient purification procedure of the protected intermediates by fluorous solid phase extraction (F-SPE).