(4R,5R)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-4-methyl-oxazolidin-2-one | 214962-93-3

• 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: (4R,5R)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-4-methyl-oxazolidin-2-one
• 英文别名: (4R,5R)-4-methyl-5-[(2R)-1-phenylmethoxypropan-2-yl]-1,3-oxazolidin-2-one
• CAS: 214962-93-3
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: UUBFFJWRADQFBV-NQBHXWOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-4-methyl-oxazolidin-2-one 在 palladium on activated charcoal 吡啶 、 盐酸 、 barium dihydroxide 、 lithium hydroxide 、 重铬酸吡啶 、 18-冠醚-6 、 氯甲磺酰氯 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 methyl (2S,3S,4R)-4-t-butyloxycarbonylamino-3-hydroxy-2-methylpentanoate
  参考文献：
  名称：

  The highly enantiocontrolled functionalization of a 2-oxazolone heterocycle by intramolecular radical-based addition. A chiral synthon for 2-amino alcohols which contain three contiguous stereocenters

  摘要：

  The intramolecular Ru(II)-catalyzed radical addition of the 2,2-dichloroacyl pendant group to the 2-oxazolone moiety followed by reductive dechlorination with (TMS)(3)SiH provides an effective tool for the formation of the chiral 2-amino alcohol synthon in a completely regio- and stereocontrolled manner. The prepared synthon is useful in the preparation of isomers of unusual amino hydroxy acids including the key component of bleomycins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01515-9
• 作为产物：
  描述：

  3-Benzyloxy-2,2-dichloro-propionic acid 2-[(1R,2S,4S)-7,7-dimethyl-1-(2-oxo-oxazole-3-carbonyl)-bicyclo[2.2.1]hept-2-yloxy]-ethyl ester 在 甲醇 、 锂硼氢 、 tris(triphenylphosphine)ruthenium(II) chloride 、 三乙基硼 、 三(三甲基硅基)硅烷 、 三氟化硼乙醚 、 甲基锂 、 三正丁基氢锡 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 120.0h， 生成 (4R,5R)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-4-methyl-oxazolidin-2-one
  参考文献：
  名称：

  The highly enantiocontrolled functionalization of a 2-oxazolone heterocycle by intramolecular radical-based addition. A chiral synthon for 2-amino alcohols which contain three contiguous stereocenters

  摘要：

  The intramolecular Ru(II)-catalyzed radical addition of the 2,2-dichloroacyl pendant group to the 2-oxazolone moiety followed by reductive dechlorination with (TMS)(3)SiH provides an effective tool for the formation of the chiral 2-amino alcohol synthon in a completely regio- and stereocontrolled manner. The prepared synthon is useful in the preparation of isomers of unusual amino hydroxy acids including the key component of bleomycins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01515-9

文献信息

• The highly enantiocontrolled functionalization of a 2-oxazolone heterocycle by intramolecular radical-based addition. A chiral synthon for 2-amino alcohols which contain three contiguous stereocenters
  作者：Toru Morita、Hirofumi Matsunaga、Eiji Sugiyama、Tadao Ishizuka、Takehisa Kunieda

  DOI：10.1016/s0040-4039(98)01515-9

  日期：1998.9

  The intramolecular Ru(II)-catalyzed radical addition of the 2,2-dichloroacyl pendant group to the 2-oxazolone moiety followed by reductive dechlorination with (TMS)(3)SiH provides an effective tool for the formation of the chiral 2-amino alcohol synthon in a completely regio- and stereocontrolled manner. The prepared synthon is useful in the preparation of isomers of unusual amino hydroxy acids including the key component of bleomycins. (C) 1998 Elsevier Science Ltd. All rights reserved.