(S)-tert-butyl 4-((S,Z)-1-(triisopropylsilyloxy)-2-(trimethylsilyl)but-2-enyl)oxazolidine-3-carboxylate | 1187449-57-5

• 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: (S)-tert-butyl 4-((S,Z)-1-(triisopropylsilyloxy)-2-(trimethylsilyl)but-2-enyl)oxazolidine-3-carboxylate
• CAS: 1187449-57-5
• 化学式: C₂₄H₄₉NO₄Si₂
• 分子量: 471.828
• InChiKey: UWBZOBCLZGJICL-SIXAVOSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-(三甲基硅基)丙炔 、 三异丙基硅烷 、 (S)-3-(tert-butoxycarbonyl)-4-formyl-1,3-oxazolidine 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以80%的产率得到(S)-tert-butyl 4-((S,Z)-1-(triisopropylsilyloxy)-2-(trimethylsilyl)but-2-enyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Diastereoselective nickel-catalyzed reductive couplings of aminoaldehydes and alkynylsilanes: application to the synthesis of d-erythro-sphingosine

  摘要：

  A strategy for the nickel-catalyzed reductive coupling of alpha-aminoaldehydes with silyl alkynes has been developed. The process proceeds with exceptional regiocontrol and diastereoselectivity. A variety of protected serinal derivatives were examined, and Garner aldehyde afforded the highest chemical yields of an easily deprotected Coupling product. Use of a C-15 alkyne allowed a direct and efficient synthesis Of D-erythro-sphingosine. With this silyl alkyne of interest, coupling reactions were most efficient when trace water was employed with THF as solvent. Using this procedure, D-erythro-sphingosine was prepared by a short sequence, wherein the alkene stereochemistry, C-3 stereocenter, and the C-3-C-4 carbon-carbon bond were all efficiently installed by the key nickel-catalyzed coupiing process. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.029