(2R,3S)-3-benzyloxy-1-(tert-butyloxycarbonyl)-2-(pyridin-2-ylthio)pyrrolidine | 847942-59-0

• 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,3S)-3-benzyloxy-1-(tert-butyloxycarbonyl)-2-(pyridin-2-ylthio)pyrrolidine
• 英文别名: tert-butyl (2R,3S)-3-phenylmethoxy-2-pyridin-2-ylsulfanylpyrrolidine-1-carboxylate
• CAS: 847942-59-0
• 化学式: C₂₁H₂₆N₂O₃S
• 分子量: 386.515
• InChiKey: JXIMNDRWTHPEQD-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-benzyloxy-1-(tert-butyloxycarbonyl)-2-(pyridin-2-ylthio)pyrrolidine 、 环己酮 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以52%的产率得到(2S,3S)-3-benzyloxy-1-(tert-butyloxycarbonyl)-2-(1-hydroxycyclohexyl)pyrrolidine
  参考文献：
  名称：

  Samarium Diiodide Promoted Generation and Asymmetric Hydroxyalkylation of N,O-Diprotected (3S)-3-Pyrrolidinol 2-Carbanions

  摘要：

  The N,O-diprotected chiral nonracemic 2-pyridyl 3-pyrrolidinol-2-yl sulfide 5a undergoes efficient SMl(2) mediated reduction to give the N,O-diprotected 3-pyrrolidinol 2-carbanion intermediate D, which reacted under Barbier-type conditions with ketones and alclehydes to afford the protected N-alpha-hydroxyalkyl-3-pyrrolidines 10b-h with excellent diastereoselectivity at the newly formed chiral center in the pyrrolidine ring. Application of the present method led to the formal asymmetric syntheses of (2R,3S)-2-hydroxymethyl-3-pyrrolidinol (2) and (2S,3S)-3hydroxyproline (12).

  DOI：

  10.1021/ol047733z
• 作为产物：
  描述：

  (S)-3-Benzyloxy-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 、 2-巯基吡啶 在 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S)-3-benzyloxy-1-(tert-butyloxycarbonyl)-2-(pyridin-2-ylthio)pyrrolidine
  参考文献：
  名称：

  Samarium Diiodide Promoted Generation and Asymmetric Hydroxyalkylation of N,O-Diprotected (3S)-3-Pyrrolidinol 2-Carbanions

  摘要：

  The N,O-diprotected chiral nonracemic 2-pyridyl 3-pyrrolidinol-2-yl sulfide 5a undergoes efficient SMl(2) mediated reduction to give the N,O-diprotected 3-pyrrolidinol 2-carbanion intermediate D, which reacted under Barbier-type conditions with ketones and alclehydes to afford the protected N-alpha-hydroxyalkyl-3-pyrrolidines 10b-h with excellent diastereoselectivity at the newly formed chiral center in the pyrrolidine ring. Application of the present method led to the formal asymmetric syntheses of (2R,3S)-2-hydroxymethyl-3-pyrrolidinol (2) and (2S,3S)-3hydroxyproline (12).

  DOI：

  10.1021/ol047733z