Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester | 473759-06-7

• 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: Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester
• 英文别名: [(3S,4S,5S,6S)-5-hydroxy-4,6-dimethyl-1-phenylmethoxy-7-tri(propan-2-yl)silyloxyheptan-3-yl] 2-methylpropanoate
• CAS: 473759-06-7
• 化学式: C₂₉H₅₂O₅Si
• 分子量: 508.814
• InChiKey: IIQCWLUVTNBLAK-XPCWZZLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester 在 咪唑 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 [Ph₃P*CuH]6 、 水 、 氟化氢吡啶 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 19.0h， 生成 Isobutyric acid (Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodec-11-enyl ester
  参考文献：
  名称：

  Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21–C34 subunit of the aplyronines

  摘要：

  The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of beta-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01217-0
• 作为产物：
  描述：

  异丁醛 、 (2S,4R,5S)-7-Benzyloxy-5-hydroxy-2,4-dimethyl-1-triisopropylsilanyloxy-heptan-3-one 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以50%的产率得到Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester
  参考文献：
  名称：

  Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21–C34 subunit of the aplyronines

  摘要：

  The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of beta-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01217-0

文献信息

• Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21–C34 subunit of the aplyronines
  作者：Ian Paterson、Simon B Blakey、Cameron J Cowden

  DOI：10.1016/s0040-4039(02)01217-0

  日期：2002.8

  The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of beta-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination. (C) 2002 Elsevier Science Ltd. All rights reserved.