4-acetoxybut-1-yl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside | 1447173-38-7

• 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: 4-acetoxybut-1-yl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: 4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybutyl acetate
• CAS: 1447173-38-7
• 化学式: C₄₇H₅₈O₁₇
• 分子量: 894.967
• InChiKey: GVNMDJNRVRIKGE-IRCDKXGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  64
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  196
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 8.0h， 生成 4-acetoxybut-1-yl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-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