tert-butyl (1R,2S,4R,5S)-3-benzyl-4-(hydroxymethyl)-6-oxa-3-azabicyclo[3.1.0]hexane-2-carboxylate | 1398228-46-0

• 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 (1R,2S,4R,5S)-3-benzyl-4-(hydroxymethyl)-6-oxa-3-azabicyclo[3.1.0]hexane-2-carboxylate
• CAS: 1398228-46-0
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: HOQRPJHCGYJLHV-CBBWQLFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4R,5R)-2-{N-benzyl-[(tert-butoxycarbonyl)methyl]iminio}-1,3-dimethyl-4,5-diphenylimidazolidin Bromide 在 碘 、 potassium carbonate 、 对甲苯磺酸 、 四甲基胍 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 34.0h， 生成 tert-butyl (1R,2S,4R,5S)-3-benzyl-4-(hydroxymethyl)-6-oxa-3-azabicyclo[3.1.0]hexane-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

文献信息

• Enantioselective Construction of a Polyhydroxylated Pyrrolidine Skeleton from 3-Vinylaziridine-2-carboxylates: Synthesis of (+)-DMDP and a Potential Common Intermediate for (+)-Hyacinthacine A₁and (+)-1-<i>epi</i>-Australine
  作者：Yukari Kondo、Noriyuki Suzuki、Masato Takahashi、Takuya Kumamoto、Hyuma Masu、Tsutomu Ishikawa

  DOI：10.1021/jo301178b

  日期：2012.9.21

  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.