(3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-penten-1-ol | 147986-47-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-penten-1-ol
• 英文别名: (3R,5S)-6-Bromo-3,5-bis[(tert-butyldimethylsilyl)oxy]-6-penten-1-ol；(3R,5S)-6-bromo-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]hept-6-en-1-ol
• CAS: 147986-47-8
• 化学式: C₁₉H₄₁BrO₃Si₂
• 分子量: 453.608
• InChiKey: HUYOCRZBQJUDPD-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-penten-1-ol 在 palladium diacetate 、 三苯基膦 18-冠醚-6 、 Zeolite 3 Angstroem 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.83h， 生成 methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate
  参考文献：
  名称：

  An efficient asymmetric synthesis of 1.alpha.,25-(OH)2 vitamin D3 A-ring synthon

  摘要：

  Chiral synthesis of the A-ring synthon 3 of 1alpha,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described. Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3, and K2CO3 gave (E)-3b and (Z)-3d, respectively. Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d. With further reactions, 1alpha,25-dihydroxyvitamin D3 (1a) was obtained.

  DOI：

  10.1021/jo00061a028
• 作为产物：
  描述：

  (3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester 在 咪唑 、 二异丁基氢化铝 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-penten-1-ol
  参考文献：
  名称：

  An efficient asymmetric synthesis of 1.alpha.,25-(OH)2 vitamin D3 A-ring synthon

  摘要：

  Chiral synthesis of the A-ring synthon 3 of 1alpha,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described. Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3, and K2CO3 gave (E)-3b and (Z)-3d, respectively. Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d. With further reactions, 1alpha,25-dihydroxyvitamin D3 (1a) was obtained.

  DOI：

  10.1021/jo00061a028