(2S,3R)-1-amino-pent-4-ene-2,3-diol | 137253-00-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3R)-1-amino-pent-4-ene-2,3-diol
• 英文别名: (2S,3R)-1-amino-4-pentene-2,3-diol；(2S,3R)-1-aminopent-4-ene-2,3-diol
• CAS: 137253-00-0
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: RIBWZLJVEAAKEZ-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-amino-pent-4-ene-2,3-diol 在 盐酸 作用下， 以 异丙醇 为溶剂， 以26 mg的产率得到(2S,3R)-1-amino-pent-4-ene-2,3-diol hydrochloride
  参考文献：
  名称：

  Total Synthesis Without Protecting Groups: Pyrrolidines and Cyclic Carbamates

  摘要：

  A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation of primary amines via a Vasella/reductive amination reaction, both performed in aqueous media.

  DOI：

  10.1021/ol802484y
• 作为产物：
  描述：

  methyl 5-deoxy-5-iodo-αlpha;/β-D-riboside 在 ammonium acetate 、 氨 、 sodium cyanoborohydride 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以91%的产率得到(2S,3R)-1-amino-pent-4-ene-2,3-diol
  参考文献：
  名称：

  A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

  摘要：

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.016

文献信息

• Regiocontrol in the synthesis of optically active amino-4-pentenediols via epoxy-4-pentenols. Novel acyclic adenosine analogues
  作者：Walter Hümmer、Tibor Gracza、Volker Jäger

  DOI：10.1016/s0040-4039(00)99506-6

  日期：1989.1
• Jaeger, Volker; Huemmer, Walter; Stahl, Ulrich, Synthesis, 1991, # 9, p. 769 - 776
  作者：Jaeger, Volker、Huemmer, Walter、Stahl, Ulrich、Gracza, Tibor

  DOI：——

  日期：——
• Kirschbaum, Bettina; Stahl, Ulrich; Jaeger, Volker, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 7-8, p. 425 - 432
  作者：Kirschbaum, Bettina、Stahl, Ulrich、Jaeger, Volker

  DOI：——

  日期：——
• Total Synthesis Without Protecting Groups: Pyrrolidines and Cyclic Carbamates
  作者：Emma M. Dangerfield、Mattie S. M. Timmer、Bridget L. Stocker

  DOI：10.1021/ol802484y

  日期：2009.2.5

  A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation of primary amines via a Vasella/reductive amination reaction, both performed in aqueous media.
• A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines
  作者：Emma M. Dangerfield、Shivali A. Gulab、Catherine H. Plunkett、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.carres.2010.03.016

  日期：2010.7

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.