(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(iodomethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine | 143006-57-9

• 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: (4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(iodomethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine
• 英文别名: (4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-[2-(iodomethyl)-3-propenyl]-2,2-dimethyl-1,3-oxazolidine；tert-butyl (4S,5S)-4-benzyl-5-[2-(iodomethyl)prop-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 143006-57-9
• 化学式: C₂₁H₃₀INO₃
• 分子量: 471.379
• InChiKey: PKLIYKNGVAKHLH-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(iodomethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine 在 铂 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 、 氧气 、 boron trifluoride diacetate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 53.0h， 生成 (2R,4S,5S)-N,2-dibenzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanamide
  参考文献：
  名称：

  A stereoselective method for the preparation of HIV-1 protease inhibitors based on the Lewis acid mediated reaction of allylsilanes and N-Boc .alpha.-amino aldehydes

  摘要：

  DOI：

  10.1021/jo00045a045
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 三氟化硼乙醚 、 对甲苯磺酸 、 sodium iodide 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 63.0h， 生成 (4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(iodomethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Stereoselective "Ene" Reaction of Allylsilanes with Amino Aldehydes. An Application to the Synthesis of Potential HIV-1 Protease Inhibitors

  摘要：

  2-Substituted 3-(trimethylsilyl)-1-propenes react with N-Boc-alpha-amino aldehydes in the presence of BF3.OEt(2) to give homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The reaction gives a predominance of the syn products, but 2-(chloromethyl)-3-(trimethylsilyl)-1-propene (5) exhibits a higher stereoselectivity with respect to other analogous allylsilanes. We hypothesize that this selectivity is due to an ''ene'' reaction followed by desilylation in the reaction medium (BF3.OEt(2), CHCl3). This reaction shows applicability to the synthesis of potential HIV-1 protease inhibitors. The preparation of compound 3, which has a structure related to the potent inhibitor L-682,679, is described.

  DOI：

  10.1021/jo00093a006

文献信息

• DAniello Fabiana, Mann Andre, Mattii Duccio, Taddei Maurizio, J. Org. Chem, 59 (1994) N 14, S 3762- 3768
  作者：DAniello Fabiana, Mann Andre, Mattii Duccio, Taddei Maurizio

  DOI：——

  日期：——
• Stereoselective "Ene" Reaction of Allylsilanes with Amino Aldehydes. An Application to the Synthesis of Potential HIV-1 Protease Inhibitors
  作者：Fabiana D'Aniello、Andre Mann、Duccio Mattii、Maurizio Taddei

  DOI：10.1021/jo00093a006

  日期：1994.7

  2-Substituted 3-(trimethylsilyl)-1-propenes react with N-Boc-alpha-amino aldehydes in the presence of BF3.OEt(2) to give homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The reaction gives a predominance of the syn products, but 2-(chloromethyl)-3-(trimethylsilyl)-1-propene (5) exhibits a higher stereoselectivity with respect to other analogous allylsilanes. We hypothesize that this selectivity is due to an ''ene'' reaction followed by desilylation in the reaction medium (BF3.OEt(2), CHCl3). This reaction shows applicability to the synthesis of potential HIV-1 protease inhibitors. The preparation of compound 3, which has a structure related to the potent inhibitor L-682,679, is described.
• A stereoselective method for the preparation of HIV-1 protease inhibitors based on the Lewis acid mediated reaction of allylsilanes and N-Boc .alpha.-amino aldehydes
  作者：Fabiana D'Aniello、Maurizio Taddei

  DOI：10.1021/jo00045a045

  日期：1992.9