methyl (R)-2-[(tert-butyldiphenylsiloxy)methyl]butanoate | 1321530-52-2

• 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: methyl (R)-2-[(tert-butyldiphenylsiloxy)methyl]butanoate
• 英文别名: (R)-methyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)butanoate；methyl (2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]butanoate
• CAS: 1321530-52-2
• 化学式: C₂₂H₃₀O₃Si
• 分子量: 370.564
• InChiKey: QWASXBBLLWKLAS-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (R)-2-[(tert-butyldiphenylsiloxy)methyl]butanoate 在 tetra-n-propylammonium perruthenate. 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.42h， 生成 (R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)butanal
  参考文献：
  名称：

  Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C

  摘要：

  Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation In high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrublelione C, which led to the assignment of the configuration of the natural product as (R).

  DOI：

  10.1021/ol201692h
• 作为产物：
  描述：

  methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate 在 C₃₁H₄₂IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、7.5 MPa 条件下， 反应 2.0h， 生成 methyl (S)-2-[(tert-butyldiphenylsiloxy)methyl]butanoate 、 methyl (R)-2-[(tert-butyldiphenylsiloxy)methyl]butanoate
  参考文献：
  名称：

  Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C

  摘要：

  Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation In high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrublelione C, which led to the assignment of the configuration of the natural product as (R).

  DOI：

  10.1021/ol201692h

文献信息

• Catalytic Enantioselective Total Synthesis of (–)-Pyridovericin
  作者：Karl Gademann、Fabian Schmid、Maurizio Bernasconi、Henning Jessen、Andreas Pfaltz

  DOI：10.1055/s-0033-1340868

  日期：——

  The first enantioselective catalytic total synthesis of (-)-pyridovericin is reported. The key steps involve a modified HWE reaction under aqueous conditions and an asymmetric iridium-catalyzed hydrogenation. This resulted in a highly modular and stereoselective approach that delivered the target natural product in high yield and stereoselectivity.
• Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C
  作者：Henning J. Jessen、Andreas Schumacher、Fabian Schmid、Andreas Pfaltz、Karl Gademann

  DOI：10.1021/ol201692h

  日期：2011.8.19

  Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation In high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrublelione C, which led to the assignment of the configuration of the natural product as (R).