(S)-(+)-trans-5-benzyloxy-4-[(triisopropylsilyl)amino]-pent-2-enoic acid ethyl ester | 1006035-94-4

• 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: (S)-(+)-trans-5-benzyloxy-4-[(triisopropylsilyl)amino]-pent-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4R)-5-phenylmethoxy-4-[tri(propan-2-yl)silylamino]pent-2-enoate
• CAS: 1006035-94-4
• 化学式: C₂₃H₃₉NO₃Si
• 分子量: 405.653
• InChiKey: AOIYVLISALCSKZ-JXVRESAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-trans-5-benzyloxy-4-[(triisopropylsilyl)amino]-pent-2-enoic acid ethyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 以66%的产率得到(S)-(+)-反式-5-苄氧基-4-氨基-2-戊烯酸乙酯
  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：

  (+)-N-(triisopropylsilyl)-O-benzyl-L-serinaldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 四氢呋喃 为溶剂， 反应 12.0h， 以85%的产率得到(S)-(+)-trans-5-benzyloxy-4-[(triisopropylsilyl)amino]-pent-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