(S)-(+)-trans-6-methylsulfanyl-4-amino-2-hexenoic acid ethyl ester | 1006036-01-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-(+)-trans-6-methylsulfanyl-4-amino-2-hexenoic acid ethyl ester
• 英文别名: ethyl (E,4S)-4-amino-6-methylsulfanylhex-2-enoate
• CAS: 1006036-01-6
• 化学式: C₉H₁₇NO₂S
• 分子量: 203.305
• InChiKey: UYMPBTODUONMOX-WTSVBCDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-trans-6-methylsulfanyl-4-amino-2-hexenoic acid ethyl ester 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-trans-6-(methylsulfanyl)-4-[((R)-α-methoxy-α-(trifluoromethyl)phenylacetyl)amino]-hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

  摘要：

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.

  DOI：

  10.1021/ol7028993
• 作为产物：
  描述：

  (S)-(+)-trans-6-methylsulfanyl-4-[(triisopropylsilyl)amino]-2-hexenoic acid ethyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 以62%的产率得到(S)-(+)-trans-6-methylsulfanyl-4-amino-2-hexenoic acid ethyl ester
  参考文献：
  名称：

  Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

  摘要：

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.

  DOI：

  10.1021/ol7028993

文献信息

• Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids
  作者：Buddy Soto-Cairoli、Jorge Justo de Pomar、John A. Soderquist

  DOI：10.1021/ol7028993

  日期：2008.1.1

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.