(1S,2S,6S)-2-Carboxymethyl-6-[methyl-((S)-1-phenyl-ethyl)-amino]-cyclohexanecarboxylic acid 1-ethyl-propyl ester | 915295-95-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2S,6S)-2-Carboxymethyl-6-[methyl-((S)-1-phenyl-ethyl)-amino]-cyclohexanecarboxylic acid 1-ethyl-propyl ester
• CAS: 915295-95-3
• 化学式: C₂₃H₃₅NO₄
• 分子量: 389.535
• InChiKey: GKYCBKNZBTWSMF-UZSDIVCKSA-N

反应信息

• 作为反应物：
  描述：

  (1S,2S,6S)-2-Carboxymethyl-6-[methyl-((S)-1-phenyl-ethyl)-amino]-cyclohexanecarboxylic acid 1-ethyl-propyl ester 在 双硫氧吡啶 、 叔丁基硫醇 、 三苯基膦 作用下， 以51%的产率得到(1S,2R,6S)-2-Methyl-6-[methyl-((S)-1-phenyl-ethyl)-amino]-cyclohexanecarboxylic acid 1-ethyl-propyl ester
  参考文献：
  名称：

  Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate

  摘要：

  An expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester followed by a 6-exo-trig cyclisation of the thus formed enolate. Cope elimination protocol of the cyclic adduct affords, depending on the lithium amide used, the corresponding nitro-compound or the expected cyclohexene derivative. The methyl group attached to the cyclohexane ring is achieved by selective ester hydrolysis and subsequent Barton decarboxylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.048
• 作为产物：
  描述：

  (1S,2S,6S)-2-(1-Ethyl-propoxycarbonylmethyl)-6-[methyl-((S)-1-phenyl-ethyl)-amino]-cyclohexanecarboxylic acid 1-ethyl-propyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以79%的产率得到(1S,2S,6S)-2-Carboxymethyl-6-[methyl-((S)-1-phenyl-ethyl)-amino]-cyclohexanecarboxylic acid 1-ethyl-propyl ester
  参考文献：
  名称：

  Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate

  摘要：

  An expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester followed by a 6-exo-trig cyclisation of the thus formed enolate. Cope elimination protocol of the cyclic adduct affords, depending on the lithium amide used, the corresponding nitro-compound or the expected cyclohexene derivative. The methyl group attached to the cyclohexane ring is achieved by selective ester hydrolysis and subsequent Barton decarboxylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.048