(3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxybutanoic acid | 648433-10-7

• 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: (3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxybutanoic acid
• CAS: 648433-10-7
• 化学式: C₄₇H₅₄O₉Si
• 分子量: 791.026
• InChiKey: LRMLTKHJQSXANS-ZUBDLPMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxybutanoic acid 在 4-二甲氨基吡啶 、 D-青霉胺 、 potassium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以37%的产率得到(1S,3S,8R,9R,10S,11R,12R,14S,19S,20S,21R,22S)-9,10,11,20,21,22-Hexakis-benzyloxy-3,14-bis-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,13,17,23,24-hexaoxa-tricyclo[17.3.1.1^8,12]tetracosane-5,16-dione
  参考文献：
  名称：

  A short access to the macrocyclic core of cycloviracin and glucolipsin

  摘要：

  The macrocyclic core of cycloviracin and glucolipsin has been synthesised in ten steps from levoglucosan and (S)-(-)-dimethyl malate. The limited number of steps to obtain this macrolide makes it a valuable procedure for the synthesis of analogues of cycloviracin and glucolipsin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.047
• 作为产物：
  描述：

  6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 在 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxybutanoic acid
  参考文献：
  名称：

  A short access to the macrocyclic core of cycloviracin and glucolipsin

  摘要：

  The macrocyclic core of cycloviracin and glucolipsin has been synthesised in ten steps from levoglucosan and (S)-(-)-dimethyl malate. The limited number of steps to obtain this macrolide makes it a valuable procedure for the synthesis of analogues of cycloviracin and glucolipsin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.047

文献信息

• A short access to the macrocyclic core of cycloviracin and glucolipsin
  作者：Vincent Bailliez、Renata M. de Figueiredo、Alain Olesker、Jeannine Cleophax

  DOI：10.1016/j.tetlet.2003.10.047

  日期：2003.12

  The macrocyclic core of cycloviracin and glucolipsin has been synthesised in ten steps from levoglucosan and (S)-(-)-dimethyl malate. The limited number of steps to obtain this macrolide makes it a valuable procedure for the synthesis of analogues of cycloviracin and glucolipsin. (C) 2003 Elsevier Ltd. All rights reserved.