(2S,4R)-benzyl 4-allyl-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylate | 951172-59-1

• 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: (2S,4R)-benzyl 4-allyl-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylate
• 英文别名: benzyl (2S,4R)-4-methyl-5-oxo-2-phenyl-4-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 951172-59-1
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: NSRWBOVKKMAQPX-GHTZIAJQSA-N

物化性质

• 沸点：
  523.6±50.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-benzyl 4-allyl-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylate 在 劳森试剂 、 lithium hydroxide 、 sodium cyanoborohydride 、 臭氧 、 溶剂黄146 、 mercury dichloride 、 lithium hexamethyldisilazane 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 142.75h， 生成 (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene
  参考文献：
  名称：

  Preparation of Diazabicyclo[4.3.0]nonene-Based Peptidomimetics

  摘要：

  Several functionalized diazabicyclo[4.3.0]nonenes and other heterocycles have been prepared as potential peptidomimetic scaffolds. A novel and efficient method has been developed for the preparation of N-substituted gamma-lactams 13. Preparation of amidine-containing 1,5-diazabicyclo[4.3.0]nonenes 43 and 44 has been achieved through Hg-mediated cyclization of the precursor N-aminopropyl-gamma-thiolactams and subsequent functional group manipulation. Bicycle 43 represents a novel scaffold for potential peptide turn mimetics, whereas 44 could potentially be employed as an alpha-helix template attached to the C-terminus of peptides. These compounds are novel additions to the current range of small-molecule constrained peptidomimetics.

  DOI：

  10.1021/jo071074x
• 作为产物：
  描述：

  氯甲酸苄酯 在 氯化亚砜 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 23.83h， 生成 (2S,4R)-benzyl 4-allyl-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylate
  参考文献：
  名称：

  [EN] PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF
  [FR] COMPOSÉS PEPTIDOMIMÉTIQUES ET CONJUGUÉS ANTICORPS-MÉDICAMENT DE CEUX-CI

  摘要：

  公开号：

  WO2015095227A3

文献信息

• Stereoselective Synthesis of (<i>R</i>)-3-Methylthalidomide by Piperidin-2-one Ring Assembly Approach
  作者：Shyam Raj Yadav、Vinay Shankar Tiwari、Wahajul Haq

  DOI：10.1002/chir.22474

  日期：2015.9

  A simple and stereoselective synthesis of 3‐methylthalidomide, a configurationally stable thalidomide analog, is presented. Herein we describe the synthesis of (R)‐3‐methylthalidomide starting from (S)‐alanine by piperidin‐2‐one ring assembly approach in high yield and enantiomeric purity without using a chiral auxiliary or reagent. Starting from (R)‐alanine, the corresponding (S)‐3‐methylthalidomide

  本文介绍了一种构型稳定的沙利度胺类似物3-甲基沙利度胺的简单且立体选择性的合成方法。本文中，我们描述了通过哌啶-2-酮一环组装方法从（S）-丙氨酸开始以（S）-丙氨酸为原料合成（R）-3-甲基沙利度胺的方法，无需使用手性助剂或试剂即可获得高收率和对映体纯度。从（R）-丙氨酸开始，可以使用相同的方法制备相应的（S）-3-甲基沙利度胺。手性27：619–624，2015。©2015 Wiley Periodicals，Inc.
• Synthesis of 4-hydroxy-2-methylproline derivatives via pyrrolidine ring assembly: chromatographic resolution and diastereoselective synthesis approaches
  作者：Vinay Shankar Tiwari、Raghavendra Murugula、Shyam Raj Yadav、Wahajul Haq

  DOI：10.1016/j.tetasy.2016.07.001

  日期：2016.10

  4-Hydroxy-2-methylproline diastereomers are successfully prepared without the use of an external chiral auxiliary. Dihydroxylation of the key intermediate 2 resulted in lactone 4 as a mixture of diastereomers in good yield. Mesylation, hydrogenation and concomitant intramolecular cyclization of 4 led to the formation of both (2R,4R)- and (2R,4S)-4-hydroxy-2-methylprolines as a mixture of diastereomers. Appropriate protection followed by chromatographic separation resulted in isolation of both cis- and trans-diastereomers in enantiomerically pure form and in equal quantity. In subsequent experiments, the synthesis of the more challenging diastereomers (2R,4R)- and (2S,4S)-4-hydroxy-2-methylproline was achieved by diastereoselective iodolactonization of (R)- or (S)-allylalanine obtained after hydrolysis of intermediate 2, followed by pyrrolidine ring closer under mild alkaline conditions. After selective protection and deprotection, Fmoc-(2R,4R)-alpha-Me-Hyp(Bu-t)-OH 14, a building block suitable for solid phase peptide synthesis was obtained. (C) 2016 Elsevier Ltd. All rights reserved.