octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside | 187140-01-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside
• CAS: 187140-01-8
• 化学式: C₃₃H₅₉FO₈Si₂
• 分子量: 658.996
• InChiKey: YQKFFDWEDIHMKD-UHHVIOASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  44.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  103.68
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside 、 3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl tricholoacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以81%的产率得到octyl (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-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：

  octyl α-D-mannopyranoside 在 吡啶 、 咪唑 、 氢氟酸 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.42h， 生成 octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-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