(2S,3S,4S)-2-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-phenylsulfanyl-pentanoic acid methyl ester | 688364-62-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,3S,4S)-2-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-phenylsulfanyl-pentanoic acid methyl ester
• 英文别名: methyl (2S,3S,4S)-2-bromo-3-[tert-butyl(dimethyl)silyl]oxy-4-methyl-5-phenylsulfanylpentanoate
• CAS: 688364-62-7
• 化学式: C₁₉H₃₁BrO₃SSi
• 分子量: 447.509
• InChiKey: FZRLZXNVDIJDAN-PVAVHDDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-phenylsulfanyl-pentanoic acid methyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以65%的产率得到(2R,3S,4S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-phenylsulfanyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucines

  摘要：

  A stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucine is disclosed. The key step of the reaction sequence involves, stereo- and regioselective bromohydration of 7, using a brominating agent derived in situ from N-bromosuccinimide and 2,6-lutidine, via intramolecular sulfinyl group participation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.117
• 作为产物：
  描述：

  methyl 4-methyl-5-phenylsulfanyl-(E,4S)-2-pentenoate 在 2,6-二甲基吡啶 、 sodium periodate 、 N-溴代丁二酰亚胺(NBS) 、 titanium(III) chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 9.5h， 生成 (2S,3S,4S)-2-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-phenylsulfanyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucines

  摘要：

  A stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucine is disclosed. The key step of the reaction sequence involves, stereo- and regioselective bromohydration of 7, using a brominating agent derived in situ from N-bromosuccinimide and 2,6-lutidine, via intramolecular sulfinyl group participation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.117

文献信息

• Stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucines
  作者：Sadagopan Raghavan、K.A. Tony

  DOI：10.1016/j.tetlet.2004.01.117

  日期：2004.3

  A stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucine is disclosed. The key step of the reaction sequence involves, stereo- and regioselective bromohydration of 7, using a brominating agent derived in situ from N-bromosuccinimide and 2,6-lutidine, via intramolecular sulfinyl group participation. (C) 2004 Elsevier Ltd. All rights reserved.