(2S,3S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)-4-phenylbutyl methanesulfonate | 1174892-47-7

• 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: (2S,3S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)-4-phenylbutyl methanesulfonate
• CAS: 1174892-47-7
• 化学式: C₂₂H₃₉NO₆SSi
• 分子量: 473.706
• InChiKey: FIFWAYVWTBCJJR-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)-4-phenylbutyl methanesulfonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以130 mg的产率得到1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯
  参考文献：
  名称：

  Stereoselective Synthesis ofanti-N-Protected 3-Amino-1,2-epoxides by Nucleophilic Addition toN-tert-Butanesulfinyl Imine of a Glyceraldehyde Synthon^†

  摘要：

  A di-O-TBS protected glyceraldellyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction Of various R groups. The Ellman adducts were converted to useful Multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2-epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.

  DOI：

  10.1021/jo900643b
• 作为产物：
  描述：

  tert-butyl (2S,3S)-3-(tertbutyldimethylsilyloxy)-4-hydroxy-1-phenylbutan-2-ylcarbamate 、 甲基磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以370 mg的产率得到(2S,3S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)-4-phenylbutyl methanesulfonate
  参考文献：
  名称：

  Stereoselective Synthesis ofanti-N-Protected 3-Amino-1,2-epoxides by Nucleophilic Addition toN-tert-Butanesulfinyl Imine of a Glyceraldehyde Synthon^†

  摘要：

  A di-O-TBS protected glyceraldellyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction Of various R groups. The Ellman adducts were converted to useful Multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2-epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.

  DOI：

  10.1021/jo900643b