tert-butyl (2S,3S)-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-2-carboxylate | 1398227-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S,3S)-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-2-carboxylate
• 英文别名: tert-butyl (2S,3S)-1-benzyl-3-[(E)-3-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]aziridine-2-carboxylate
• CAS: 1398227-90-1
• 化学式: C₂₃H₃₇NO₃Si
• 分子量: 403.637
• InChiKey: VPOGEZCCOXCXKT-OYGBFJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴甲苯 在 四甲基胍 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 28.5h， 生成 tert-butyl (2S,3R)-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-2-carboxylate 、 tert-butyl (2R,3R)-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-2-carboxylate 、 tert-butyl (2S,3S)-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-2-carboxylate
  参考文献：
  名称：

  Enantioselective Construction of a Polyhydroxylated Pyrrolidine Skeleton from 3-Vinylaziridine-2-carboxylates: Synthesis of (+)-DMDP and a Potential Common Intermediate for (+)-Hyacinthacine A₁and (+)-1-epi-Australine

  摘要：

  We report an enantioselective synthesis of the polyhydroxylated pyrrolidine alkaloid (+)-DMDP. The key steps in the synthesis were guanidinium ylide mediated asymmetric aziridination, stereospecific ring opening of trans-3-vinylaziridine-2-carboxylate with an oxygen nucleophile, iodine-mediated 5-endo-trig amino cyclization, and Prevost displacement. In addition, a potential common intermediate for the polyhydroxylated pyrrolizidine alkaloids (+)-hyacinthacine A(1) and (+)-1-epi-australine was synthesized from a diastereoisomeric cis-aziridine coformed in the asymmetric aziridination using the same strategy. A rationale for the diastereoselectivity observed for the iodine-mediated amino cyclization reactions is proposed on the basis of the heats of formation of the products.

  DOI：

  10.1021/jo301178b