(R)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester | 433235-59-7

• 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: (R)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
• 英文别名: benzyl (4R)-4-[(R)-[(3R,7aR)-3-tert-butyl-1-oxo-3,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazol-7a-yl]-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 433235-59-7
• 化学式: C₂₄H₃₄N₂O₆
• 分子量: 446.544
• InChiKey: MHQOEPCCNHZCKB-ZVVFGRKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 copper(l) iodide 、 硫酸 、 过氧化脲素 、 甲基三氧化铼(VII) 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl (2R,5R)-2-[(1S,2R)-3-[tert-butyl(diphenyl)silyl]oxy-2-(phenylmethoxycarbonylamino)-1-trimethylsilyloxypropyl]-5-[(2S)-2-[(3,5-dichloro-4-phenylmethoxybenzoyl)amino]-3-oxo-3-phenylmethoxypropyl]-1-hydroxypyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of the proposed structure and revision of stereochemistry of kaitocephalin

  摘要：

  A stereoselective total synthesis of the proposed structure of kaitocephalin (1) was accomplished starting from L-proline and D- and L-serines. How ever, its H-1 NMR spectral data and retention time oil HPLC were not identical with those of authentic natural kaitocephalin. The revised stereochemistry of natural kaitocephalin. (2R)-isomer (16), was inferred from further experiments employing diastereomers and model compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02254-7
• 作为产物：
  描述：

  (R)-4-甲酰基-2,2-二甲基噁唑啉-3-羧酸苄酯 、 (2R,5S)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 、 (R)-4-[(S)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the proposed structure and revision of stereochemistry of kaitocephalin

  摘要：

  A stereoselective total synthesis of the proposed structure of kaitocephalin (1) was accomplished starting from L-proline and D- and L-serines. How ever, its H-1 NMR spectral data and retention time oil HPLC were not identical with those of authentic natural kaitocephalin. The revised stereochemistry of natural kaitocephalin. (2R)-isomer (16), was inferred from further experiments employing diastereomers and model compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02254-7