8-(tert-butyldiphenylsilyloxy)oct-1-yl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside | 1447173-29-6

• 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: 8-(tert-butyldiphenylsilyloxy)oct-1-yl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside
• 英文别名: tert-butyl-diphenyl-[8-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(trityloxymethyl)oxan-2-yl]oxyoctoxy]silane
• CAS: 1447173-29-6
• 化学式: C₇₀H₇₈O₇Si
• 分子量: 1059.47
• InChiKey: STLYQEYHSDSJBJ-YTLFJISXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.41
• 重原子数：
  78
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(tert-butyldiphenylsilyloxy)oct-1-yl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以88%的产率得到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 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 Hg⁽¹⁺⁾*2CN^(1-) 、 sodium methylate 、 sodium hydride 、 mercury dibromide 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 、 mineral oil 为溶剂， 反应 56.5h， 生成 8-(tert-butyldiphenylsilyloxy)oct-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

文献信息

• Surface-Tethered Iterative Carbohydrate Synthesis: A Spacer Study
  作者：N. Vijaya Ganesh、Kohki Fujikawa、Yih Horng Tan、Swati S. Nigudkar、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1021/jo400095u

  日期：2013.7.19

  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.