1-O-tert-butyldiphenylsilyl-2-O-(2-benzylcarbamate-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-sn-glycerol | 1354914-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-tert-butyldiphenylsilyl-2-O-(2-benzylcarbamate-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-sn-glycerol
• CAS: 1354914-16-1
• 化学式: C₅₇H₆₅NO₉Si
• 分子量: 936.23
• InChiKey: HHRAVTCWBVFIDI-MKMSVVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.56
• 重原子数：
  68.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102.94
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyldiphenylsilyl-2-O-(2-benzylcarbamate-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-sn-glycerol 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-2-O-(2-benzylcarbamate-3,4,6-tri-O-benzyl-2-deoxy-α-Dglucopyranosyl)-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-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol 在 碳酸氢钠 、 三甲基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 5.5h， 生成 1-O-tert-butyldiphenylsilyl-2-O-(2-benzylcarbamate-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-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