tert-butyl (2S,3S,4E)-2-benzylamino-3,6-dihydroxyhex-4-enoate | 1398228-23-3

• 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,4E)-2-benzylamino-3,6-dihydroxyhex-4-enoate
• 英文别名: tert-butyl (E,2S,3S)-2-(benzylamino)-3,6-dihydroxyhex-4-enoate
• CAS: 1398228-23-3
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: CUYXYWBFCFTMHF-IDZXHDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S,4E)-2-benzylamino-3,6-dihydroxyhex-4-enoate 在 碘 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以62%的产率得到tert-butyl (2S,3R,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-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
• 作为产物：
  描述：

  tert-butyl (2S,3R)-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-2-carboxylate 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以84%的产率得到tert-butyl (2S,3S,4E)-2-benzylamino-3,6-dihydroxyhex-4-enoate
  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.