(3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-heptenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester | 148023-11-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-heptenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester
• 英文别名: [(1S)-2-hydroxy-1,2,2-triphenylethyl] (3R,5S)-6-bromo-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]hept-6-enoate
• CAS: 148023-11-4
• 化学式: C₃₉H₅₅BrO₅Si₂
• 分子量: 739.938
• InChiKey: NRAGKSHGVUXVNO-ZHAMFGDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.68
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-heptenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester 在 palladium diacetate 、 三苯基膦 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 <3S-(1Z,3α,5α)>-<3,5-Bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetic acid methyl ester
  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：

  (S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester 在 咪唑 、 Zeolite 3 Angstroem 、 二异丁基氢化铝 、 pyridinium chlorochromate 、 magnesium bromide 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 (3R,5S)-6-Bromo-3,5-bis<(tert-butyldimethylsilyl)oxy>-6-heptenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester
  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