tert-butyl (2R,3R,6S,αR)-3-phenyl-4-(α-methylbenzyl)-6-methylthiomorpholine-2-carboxylate | 900518-23-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2R,3R,6S,αR)-3-phenyl-4-(α-methylbenzyl)-6-methylthiomorpholine-2-carboxylate
• 英文别名: tert-butyl (2R,3R,6S)-6-methyl-3-phenyl-4-[(1R)-1-phenylethyl]thiomorpholine-2-carboxylate
• CAS: 900518-23-2
• 化学式: C₂₄H₃₁NO₂S
• 分子量: 397.582
• InChiKey: GTCFJLDJLKMBMN-XHIHJMKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3R,6S,αR)-3-phenyl-4-(α-methylbenzyl)-6-methylthiomorpholine-2-carboxylate 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以65%的产率得到tert-butyl (2S,3R,6S,αR)-3-phenyl-4-(α-methylbenzyl)-6-methylthiomorpholine-2-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of α-mercapto-β-amino acid derivatives: application to the synthesis of polysubstituted thiomorpholines

  摘要：

  Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.004
• 作为产物：
  描述：

  tert-butyl (3R,αR)-2-tert-butylthio-3-[N-allyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 14.5h， 生成 tert-butyl (2R,3R,6S,αR)-3-phenyl-4-(α-methylbenzyl)-6-methylthiomorpholine-2-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of α-mercapto-β-amino acid derivatives: application to the synthesis of polysubstituted thiomorpholines

  摘要：

  Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.004