(S)-tert-butyl 4-((R,E)-1-hydroxybut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate | 1187449-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-tert-butyl 4-((R,E)-1-hydroxybut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(E,1R)-1-hydroxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1187449-59-7
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: KSOFNBWVFINBSK-IAYMVZNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-十五碳烯 、 (S)-tert-butyl 4-((R,E)-1-hydroxybut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以82%的产率得到(2S,3R,4E)-3-(tert-butoxycarbonyl)-4-(1-hydroxy-hexadec-2-enyl)-2,2-dimethyloxazolidine
  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
• 作为产物：
  描述：

  (S)-tert-butyl 2,2-dimethyl-4-((S,Z)-1-(triisopropylsilyloxy)-2-(trimethylsilyl)but-2-enyl)oxazolidine-3-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以91%的产率得到(S)-tert-butyl 4-((R,E)-1-hydroxybut-2-enyl)-2,2-dimethyloxazolidine-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

文献信息

• METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS
  申请人：Cerenis Therapeutics Holding SA

  公开号：EP3363805B1

  公开（公告）日：2020-12-16
• US9643915B2
  申请人：——

  公开号：US9643915B2

  公开（公告）日：2017-05-09
• US9708354B2
  申请人：——

  公开号：US9708354B2

  公开（公告）日：2017-07-18
• Diastereoselective nickel-catalyzed reductive couplings of aminoaldehydes and alkynylsilanes: application to the synthesis of d-erythro-sphingosine
  作者：Kanicha Sa-ei、John Montgomery

  DOI：10.1016/j.tet.2009.05.029

  日期：2009.8

  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.