(2R,3R,E)-6-(tert-butyldimethylsilyloxy)-2-hydroxy-3-((4-methoxybenzyloxy)methyl)-2-methylhex-4-enoic acid | 1187335-29-0

• 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: (2R,3R,E)-6-(tert-butyldimethylsilyloxy)-2-hydroxy-3-((4-methoxybenzyloxy)methyl)-2-methylhex-4-enoic acid
• 英文别名: (E,2R,3R)-6-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3-[(4-methoxyphenyl)methoxymethyl]-2-methylhex-4-enoic acid
• CAS: 1187335-29-0
• 化学式: C₂₂H₃₆O₆Si
• 分子量: 424.61
• InChiKey: QGOFROQXIHNKSX-HWOYEPTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S,E)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-yl 2-oxopropanoate 在 1,1-di-tert-butyl-2,2-dimethylsilirane 、 silver(I) 4-methylbenzenesulfonate 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以80%的产率得到(2R,3R,E)-6-(tert-butyldimethylsilyloxy)-2-hydroxy-3-((4-methoxybenzyloxy)methyl)-2-methylhex-4-enoic acid
  参考文献：
  名称：

  Silylene transfer to α-keto esters and application to the synthesis of γ-lactones

  摘要：

  Disubstituted alpha-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to alpha-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The alpha-hydroxy acid products can be converted into gamma-lactones using a variety of lactonization conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.066

文献信息

• Silylene transfer to α-keto esters and application to the synthesis of γ-lactones
  作者：Brett E. Howard、K.A. Woerpel

  DOI：10.1016/j.tet.2009.05.066

  日期：2009.8

  Disubstituted alpha-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to alpha-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The alpha-hydroxy acid products can be converted into gamma-lactones using a variety of lactonization conditions. (C) 2009 Elsevier Ltd. All rights reserved.