3-O-allyl-2-O-(2-azido-2-deoxy-6-O-[4,4'-dimethoxytrityl]-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol | 1354914-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-O-allyl-2-O-(2-azido-2-deoxy-6-O-[4,4'-dimethoxytrityl]-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol
• CAS: 1354914-32-1
• 化学式: C₄₉H₅₇N₃O₉Si
• 分子量: 860.092
• InChiKey: AQKLARVMHADRFO-DARATDDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  62.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  153.83
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2-O-(2-azido-2-deoxy-6-O-[4,4'-dimethoxytrityl]-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 32.0h， 生成 3-O-allyl-2-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-[4,4'-dimethoxytrityl]-α-D-glucopyranosyl)-1-O-benzyl-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：

  4,4'-双甲氧基三苯甲基氯 、 (2R,3S,4R,5R,6S)-6-[(S)-1-Allyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-5-azido-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到3-O-allyl-2-O-(2-azido-2-deoxy-6-O-[4,4'-dimethoxytrityl]-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-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