(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol | 725724-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol
• 英文别名: (2R,8R,20R)-22-[tert-butyl(diphenyl)silyl]oxy-20-[(4-methoxyphenyl)methoxy]-2-phenylmethoxydocos-10-yn-8-ol
• CAS: 725724-09-4
• 化学式: C₅₃H₇₄O₅Si
• 分子量: 819.253
• InChiKey: TUJIMTMJEWSSJH-XALPTUKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.98
• 重原子数：
  59
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol 在 Wilkinson's catalyst 、 氢气 作用下， 以 苯 为溶剂， 反应 10.0h， 以99%的产率得到(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docosan-8-ol
  参考文献：
  名称：

  Synthetic Studies on Macroviracin A:  A Rapid Construction of C₄₂ Macrocyclic Dilactone Corresponding to the Core

  摘要：

  The C-2-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C-22-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The use of potassium hydride instead of NaH caused the intramolecular cyclization, predominantly providing the corresponding monomer 26. The acid 3 was synthesized through a series of reactions such as the coupling reaction of acetylene 5 and oxirane 6, stereoselective glycosidation with the trichloroacetimidate method, and Jones oxidation.

  DOI：

  10.1021/jo0496392
• 作为产物：
  描述：

  (R)-3-(苄氧基)丁-1-醇 在 吡啶 、 正丁基锂 、 (R,R)-1,2-cyclohexanediamine based salen cobalt 、 magnesium 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 46.0h， 生成 (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol
  参考文献：
  名称：

  Synthetic Studies on Macroviracin A:  A Rapid Construction of C₄₂ Macrocyclic Dilactone Corresponding to the Core

  摘要：

  The C-2-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C-22-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The use of potassium hydride instead of NaH caused the intramolecular cyclization, predominantly providing the corresponding monomer 26. The acid 3 was synthesized through a series of reactions such as the coupling reaction of acetylene 5 and oxirane 6, stereoselective glycosidation with the trichloroacetimidate method, and Jones oxidation.

  DOI：

  10.1021/jo0496392