(5R,7S,2Z)-8-Bromo-5,7-bis<(tert-butyldimethylsilyl)oxy>-2,8-nonadienoic acid methyl ester | 137892-15-0

• 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: (5R,7S,2Z)-8-Bromo-5,7-bis<(tert-butyldimethylsilyl)oxy>-2,8-nonadienoic acid methyl ester
• 英文别名: (5R,7S,2Z)-8-Bromo-5,7-bis[(tert-butyldimethylsilyl)oxy]-2,8-nonadienoic acid methyl ester；methyl (2Z,5R,7S)-8-bromo-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]nona-2,8-dienoate
• CAS: 137892-15-0
• 化学式: C₂₂H₄₃BrO₄Si₂
• 分子量: 507.656
• InChiKey: KGSIKTXMHIJJQB-MSODLAMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,7S,2Z)-8-Bromo-5,7-bis<(tert-butyldimethylsilyl)oxy>-2,8-nonadienoic acid methyl ester 在 Pd(PPh₃)(OAc)2 potassium carbonate 作用下， 以 乙腈 为溶剂， 以90%的产率得到methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate
  参考文献：
  名称：

  Stereoselective synthesis of 1α-hydroxyvitamin D3 A-ring synthons by palladium-catalyzed cyclization

  摘要：

  Palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates proceeded stereoselectively to give 1-alpha-hydroxyvitamin D3 A-ring synthons in good yields.

  DOI：

  10.1016/s0040-4039(00)93501-9
• 作为产物：
  描述：

  Methyl 6-Bromo-5-hydroxy-3-oxo-6-heptenoate 在 咪唑 、 tetramethylammonium borohydride 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 4.33h， 生成 (5R,7S,2Z)-8-Bromo-5,7-bis<(tert-butyldimethylsilyl)oxy>-2,8-nonadienoic 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

文献信息

• An efficient asymmetric synthesis of 1.alpha.,25-(OH)2 vitamin D3 A-ring synthon
  作者：Kazuo Nagasawa、Hideki Ishihara、Yoshiro Zako、Isao Shimizu

  DOI：10.1021/jo00061a028

  日期：1993.4

  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.
• Stereoselective synthesis of 1α-hydroxyvitamin D3 A-ring synthons by palladium-catalyzed cyclization
  作者：Kazuo Nagasawa、Yoshiro Zako、Hideki Ishihara、Isao Shimizu

  DOI：10.1016/s0040-4039(00)93501-9

  日期：1991.9

  Palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates proceeded stereoselectively to give 1-alpha-hydroxyvitamin D3 A-ring synthons in good yields.