(S,S)-2-{[2-(tert-butyldimethylsilanyloxymethyl)-phenyl]-hydroxymethyl}-2-methylpent-3-enoic acid methyl ester | 887130-22-5

• 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: (S,S)-2-{[2-(tert-butyldimethylsilanyloxymethyl)-phenyl]-hydroxymethyl}-2-methylpent-3-enoic acid methyl ester
• 英文别名: methyl (E,2S)-2-[(S)-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-hydroxymethyl]-2-methylpent-3-enoate
• CAS: 887130-22-5
• 化学式: C₂₁H₃₄O₄Si
• 分子量: 378.584
• InChiKey: HZVDPJHHIICXFL-WHXYHPJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,S)-2-{[2-(tert-butyldimethylsilanyloxymethyl)-phenyl]-hydroxymethyl}-2-methylpent-3-enoic acid methyl ester 、 异丁醛 在 tin(II) trifluoromethanesulfonate 、 四氯化锡 、 silver carbonate 作用下， 以 二氯甲烷 、 硝基甲烷 为溶剂， 反应 2.25h， 生成 (5S,6R)-6-isopropyl-3,5-dimethyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements

  摘要：

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.

  DOI：

  10.1021/ja061082f
• 作为产物：
  描述：

  methyl (E)-4-bromo-2-methyl-2-pentenoate 在 palladium diacetate 、 diethylzinc 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (S,S)-2-{[2-(tert-butyldimethylsilanyloxymethyl)-phenyl]-hydroxymethyl}-2-methylpent-3-enoic acid methyl ester
  参考文献：
  名称：

  New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements

  摘要：

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.

  DOI：

  10.1021/ja061082f

文献信息

• New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements
  作者：Yi-Hung Chen、Frank E. McDonald

  DOI：10.1021/ja061082f

  日期：2006.4.1

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.