[(2S,3aS,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-hexahydro-pyrrolo[1,2-b]isoxazol-5-yl]-carbamic acid tert-butyl ester | 267234-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: [(2S,3aS,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-hexahydro-pyrrolo[1,2-b]isoxazol-5-yl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S,3aS,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(2-hydroxyethyl)-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b][1,2]oxazol-5-yl]carbamate
• CAS: 267234-22-0
• 化学式: C₁₉H₃₈N₂O₅Si
• 分子量: 402.607
• InChiKey: JSJSUJCGOIJJRU-LVQVYYBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3aS,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-hexahydro-pyrrolo[1,2-b]isoxazol-5-yl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 [(1R,2R,7R,8aS)-1-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-octahydro-indolizin-2-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
• 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 、 苯 为溶剂， 反应 74.0h， 生成 [(2S,3aS,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-hexahydro-pyrrolo[1,2-b]isoxazol-5-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.