(2R,4R,2'R,3'S)-2-(3-methyloxiran-2-yl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester | 179471-86-4

• 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: (2R,4R,2'R,3'S)-2-(3-methyloxiran-2-yl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester
• 英文别名: ethyl (2R,4R)-2-[(2R,3S)-3-methyloxiran-2-yl]-4-phenyl-1,3-oxazolidine-3-carboxylate
• CAS: 179471-86-4
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: GTQPMGWLOLXJAV-SCUASFONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R,2'R,3'S)-2-(3-methyloxiran-2-yl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester 在 palladium dihydroxide 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 2.0h， 生成 (R)-5-Isopropyl-4-phenethyloxy-oxazolidin-2-one
  参考文献：
  名称：

  Chiral oxazolidinones from α-hydroxy oxazolidines: a new access to 1,2-amino alcohols

  摘要：

  N-Carbamoyl-alpha-hydroxy oxazolidines prepared from N-Boc-2-acyl oxazolidines or N-Boc-2-alkenyl oxazolidines, using phenyl glycinol as the chiral source, are converted into bicyclic oxazolidinones. Reactions of these compounds with different nucleophiles under conditions suitable for the production of N-acyliminium ions were studied. Allylsilane reacted very stereoselectively in all cases, and this reaction provides a new flexible entry for the preparation of enantiopure syn-2-amino alcohols, possibly bearing an additional stereocenter ex to the hydroxyl moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00414-5
• 作为产物：
  描述：

  D-苯甘氨醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (2R,4R,2'R,3'S)-2-(3-methyloxiran-2-yl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Regio- and Stereocontrolled Formation of Chiral Epoxy Oxazolidines via Bromocarbamation of N-Boc Alkenyl Oxazolidines. Application to Asymmetric Synthesis

  摘要：

  Treatment of alpha-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide an these epoxides, followed by a few functional group manipulations, eventually affords chiral beta-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.

  DOI：

  10.1021/jo962277g

文献信息

• Regio- and Stereocontrolled Formation of Chiral Epoxy Oxazolidines via Bromocarbamation of <i>N</i>-Boc Alkenyl Oxazolidines. Application to Asymmetric Synthesis
  作者：Claude Agami、François Couty、Louis Hamon、Olivier Venier

  DOI：10.1021/jo962277g

  日期：1997.4.1

  Treatment of alpha-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide an these epoxides, followed by a few functional group manipulations, eventually affords chiral beta-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.
• Chiral oxazolidinones from α-hydroxy oxazolidines: a new access to 1,2-amino alcohols
  作者：Claude Agami、Franck Amiot、François Couty、Luc Dechoux、Christophe Kaminsky、Olivier Venier

  DOI：10.1016/s0957-4166(98)00414-5

  日期：1998.11

  N-Carbamoyl-alpha-hydroxy oxazolidines prepared from N-Boc-2-acyl oxazolidines or N-Boc-2-alkenyl oxazolidines, using phenyl glycinol as the chiral source, are converted into bicyclic oxazolidinones. Reactions of these compounds with different nucleophiles under conditions suitable for the production of N-acyliminium ions were studied. Allylsilane reacted very stereoselectively in all cases, and this reaction provides a new flexible entry for the preparation of enantiopure syn-2-amino alcohols, possibly bearing an additional stereocenter ex to the hydroxyl moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.