(R)-N-((2R,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-phenylbutan-2-yl)-2-methylpropane-2-sulfinamide | 1174892-45-5

• 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: (R)-N-((2R,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-phenylbutan-2-yl)-2-methylpropane-2-sulfinamide
• 英文别名: (R)-N-[(2R,3S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-1-phenylbutan-2-yl]-2-methylpropane-2-sulfinamide
• CAS: 1174892-45-5
• 化学式: C₂₆H₅₁NO₃SSi₂
• 分子量: 513.933
• InChiKey: WPCWBTWTLVKNRK-CEFNRUSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R,E)-N-((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide 、 苄基氯化镁 在 四甲基乙二胺 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.75h， 以350 mg的产率得到(R)-N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-phenylbutan-2-yl)-2-methylpropane-2-sulfinamide
  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

文献信息

• Stereoselective Synthesis of<i>anti</i>-<i>N</i>-Protected 3-Amino-1,2-epoxides by Nucleophilic Addition to<i>N</i>-<i>tert</i>-Butanesulfinyl Imine of a Glyceraldehyde Synthon^†
  作者：Scott S. Harried、Michael D. Croghan、Matthew R. Kaller、Patricia Lopez、Wenge Zhong、Randall Hungate、Paul J. Reider

  DOI：10.1021/jo900643b

  日期：2009.8.21

  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.