8-(tert-butyldiphenylsilyloxy)oct-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 1447173-28-5

• 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: 8-(tert-butyldiphenylsilyloxy)oct-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[8-[tert-butyl(diphenyl)silyl]oxyoctoxy]oxan-2-yl]methyl benzoate
• CAS: 1447173-28-5
• 化学式: C₅₈H₆₂O₁₁Si
• 分子量: 963.209
• InChiKey: RPDMYFNOGQXWGG-DPAXTVHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.18
• 重原子数：
  70
• 可旋转键数：
  27
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8-(tert-butyldiphenylsilyloxy)oct-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium methylate 、 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 23.5h， 生成 8-hydroxyoct-1-yl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside
  参考文献：
  名称：

  Surface-Tethered Iterative Carbohydrate Synthesis: A Spacer Study

  摘要：

  Comparative study of Surface-Tethered Iterative Carbohydrate Synthesis (STICS) using HPLC-assisted experimental setup clearly demonstrates benefits of using longer spacer-anchoring systems. The use of mixed self-assembled monolayers helps provide the required space for glycosylation reaction around the immobilized glycosyl acceptor. Both extension of the spacer length and using mixed self-assembled monolayers help promote the reaction, and the beneficial effects may include moving the glycosyl acceptor further out into solution and providing additional conformational flexibility. It is possible that surface-immobilized glycosyl acceptors with a longer spacer (C8-O-C8)-lipoic acid have a higher tendency to mimic a solution-phase reaction environment than acceptors with shorter spacers.

  DOI：

  10.1021/jo400095u
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 8-((tert-butyldiphenylsilyl)oxy)octan-1-ol 在 Hg⁽¹⁺⁾*2CN^(1-) 、 mercury dibromide 作用下， 以 邻二氯苯 为溶剂， 反应 36.0h， 以92%的产率得到8-(tert-butyldiphenylsilyloxy)oct-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Surface-Tethered Iterative Carbohydrate Synthesis: A Spacer Study

  摘要：

  Comparative study of Surface-Tethered Iterative Carbohydrate Synthesis (STICS) using HPLC-assisted experimental setup clearly demonstrates benefits of using longer spacer-anchoring systems. The use of mixed self-assembled monolayers helps provide the required space for glycosylation reaction around the immobilized glycosyl acceptor. Both extension of the spacer length and using mixed self-assembled monolayers help promote the reaction, and the beneficial effects may include moving the glycosyl acceptor further out into solution and providing additional conformational flexibility. It is possible that surface-immobilized glycosyl acceptors with a longer spacer (C8-O-C8)-lipoic acid have a higher tendency to mimic a solution-phase reaction environment than acceptors with shorter spacers.

  DOI：

  10.1021/jo400095u