[(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-oxy-3,4-dihydro-2H-pyrrol-3-yl]-carbamic acid tert-butyl ester | 267234-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: [(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-oxy-3,4-dihydro-2H-pyrrol-3-yl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-1-oxido-3,4-dihydro-2H-pyrrol-1-ium-3-yl]carbamate
• CAS: 267234-09-3
• 化学式: C₁₅H₃₀N₂O₄Si
• 分子量: 330.5
• InChiKey: GMFSJEUZJIBEAL-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  76.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-oxy-3,4-dihydro-2H-pyrrol-3-yl]-carbamic acid tert-butyl ester 在 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 73.0h， 生成 Methanesulfonic acid 2-[(2S,3aS,4R,5R)-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-hexahydro-pyrrolo[1,2-b]isoxazol-2-yl]-ethyl ester
  参考文献：
  名称：

  Synthesis of enantiopure protected 3-hydroxy-4-amino pyrroline N-oxides

  摘要：

  The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02335-7
• 作为产物：
  描述：

  (3R,4S)-1-benzyl-3-amino-4-(tert-butyldimethylsilyloxy)pyrrolidine 在 palladium dihydroxide 氢气 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 [(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-oxy-3,4-dihydro-2H-pyrrol-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of enantiopure protected 3-hydroxy-4-amino pyrroline N-oxides

  摘要：

  The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02335-7

文献信息

• Synthesis of enantiopure protected 3-hydroxy-4-amino pyrroline N-oxides
  作者：Stefano Cicchi、Paola Ponzuoli、Andrea Goti、Alberto Brandi

  DOI：10.1016/s0040-4039(99)02335-7

  日期：2000.3

  The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines. (C) 2000 Elsevier Science Ltd. All rights reserved.