(1S,3S,7aR)-1-[(R)-1-Benzyloxycarbonylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-tert-butyl-dihydro-pyrrolo[1,2-c]oxazole-7a-carboxylic acid benzyl ester | 433236-91-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,3S,7aR)-1-[(R)-1-Benzyloxycarbonylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-tert-butyl-dihydro-pyrrolo[1,2-c]oxazole-7a-carboxylic acid benzyl ester
• 英文别名: benzyl (1S,3S,7aR)-3-tert-butyl-1-[(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-(phenylmethoxycarbonylamino)ethyl]-3,5,6,7-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
• CAS: 433236-91-0
• 化学式: C₄₄H₅₄N₂O₆Si
• 分子量: 735.008
• InChiKey: IQJCUZNJQLZIPF-ITILTVFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,3S,7aR)-1-[(R)-1-Benzyloxycarbonylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-tert-butyl-dihydro-pyrrolo[1,2-c]oxazole-7a-carboxylic acid benzyl ester 在 咪唑 、 copper(l) iodide 、 过氧化脲素 、 甲基三氧化铼(VII) 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 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-[(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 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 硫酸 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,3S,7aR)-1-[(R)-1-Benzyloxycarbonylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-tert-butyl-dihydro-pyrrolo[1,2-c]oxazole-7a-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

文献信息

• Synthesis of the proposed structure and revision of stereochemistry of kaitocephalin
  作者：Masayuki Okue、Hiroyuki Kobayashi、Kazuo Shin-ya、Kazuo Furihata、Yoichi Hayakawa、Haruo Seto、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/s0040-4039(01)02254-7

  日期：2002.1

  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.