tert-butyl (2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(4-cyanophenoxy)pyrrolidine-1-carboxylate | 540508-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(4-cyanophenoxy)pyrrolidine-1-carboxylate
• CAS: 540508-30-3
• 化学式: C₂₃H₃₆N₂O₄Si
• 分子量: 432.635
• InChiKey: SBUXLNQJGSVVNO-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(4-cyanophenoxy)pyrrolidine-1-carboxylate 在 4-二甲氨基吡啶 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 (2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  Studies toward a synthesis of C3-epimauritine D: construction of the macrocycle

  摘要：

  We successfully synthesized a 14-membered cyclic enamide of C3-epimauritine D from the cis-2,3-pyrrolidinediol derivative. Treatment of the pyrrolidinediol with nitrobenzonitrile in an SNAr reaction efficiently installed the desired aryl-alkyl ether linkage on the N-heterocyclic system. Macrocyclization was successfully achieved by the use of TFFH as the peptide coupling reagent in the presence of HOAt. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00278-8
• 作为产物：
  描述：

  (4R,5S)-5-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-4-hydroxy-1-<(1,1-dimethylethoxy)carbonyl>-pyrrolidin-2-one 在 dimethyl sulfide borane 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 tert-butyl (2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(4-cyanophenoxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Studies toward a synthesis of C3-epimauritine D: construction of the macrocycle

  摘要：

  We successfully synthesized a 14-membered cyclic enamide of C3-epimauritine D from the cis-2,3-pyrrolidinediol derivative. Treatment of the pyrrolidinediol with nitrobenzonitrile in an SNAr reaction efficiently installed the desired aryl-alkyl ether linkage on the N-heterocyclic system. Macrocyclization was successfully achieved by the use of TFFH as the peptide coupling reagent in the presence of HOAt. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00278-8

文献信息

• Studies toward a synthesis of C3-epimauritine D: construction of the macrocycle
  作者：Young-Ah Kim、Hyo-Nim Shin、Myoung-Soon Park、So-Hye Cho、So-Yeop Han

  DOI：10.1016/s0040-4039(03)00278-8

  日期：2003.3

  We successfully synthesized a 14-membered cyclic enamide of C3-epimauritine D from the cis-2,3-pyrrolidinediol derivative. Treatment of the pyrrolidinediol with nitrobenzonitrile in an SNAr reaction efficiently installed the desired aryl-alkyl ether linkage on the N-heterocyclic system. Macrocyclization was successfully achieved by the use of TFFH as the peptide coupling reagent in the presence of HOAt. (C) 2003 Elsevier Science Ltd. All rights reserved.