(2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester | 433237-95-7

• 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: (2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester
• 英文别名: dibenzyl (2R,5R)-5-[(2S)-2-[(3,5-dichloro-4-phenylmethoxybenzoyl)amino]-3-oxo-3-phenylmethoxypropyl]-2-[(1S,2R)-1,3-dihydroxy-2-(phenylmethoxycarbonylamino)propyl]pyrrolidine-1,2-dicarboxylate
• CAS: 433237-95-7
• 化学式: C₅₅H₅₃Cl₂N₃O₁₂
• 分子量: 1018.94
• InChiKey: DRLXVTYVWZIJGM-JJKWPWDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  72
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  199
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 在 palladium dihydroxide 4-甲氧基-四甲基哌啶氧自由基 、 sodium hypochlorite 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 kaitocephalin
  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-[(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 在 咪唑 、 4-二甲氨基吡啶 、 copper(l) iodide 、 硫酸 、 四丁基氟化铵 、 过氧化脲素 、 甲基三氧化铼(VII) 、 碳酸氢钠 、 potassium carbonate 、 氯化铵 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2R,5R)-2-((1S,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-5-[(S)-2-benzyloxycarbonyl-2-(4-benzyloxy-3,5-dichloro-benzoylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid dibenzyl 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.