N-tert-butoxycarbonyl-L-phenylalanyl-L-proline 9-fluorenylmethyl thioester | 1330059-31-8

• 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: N-tert-butoxycarbonyl-L-phenylalanyl-L-proline 9-fluorenylmethyl thioester
• CAS: 1330059-31-8
• 化学式: C₃₃H₃₆N₂O₄S
• 分子量: 556.726
• InChiKey: DCLIHYUPLYEZSU-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-phenylalanyl-L-proline 9-fluorenylmethyl thioester 在 哌啶 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Boc-L-Phe-L-Pro-SH
  参考文献：
  名称：

  In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions

  摘要：

  The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1 degrees and 2 degrees amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

  DOI：

  10.1021/ja2065158
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-L-proline 9-fluorenylmethyl thioester 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N-tert-butoxycarbonyl-L-phenylalanyl-L-proline 9-fluorenylmethyl thioester
  参考文献：
  名称：

  In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions

  摘要：

  The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1 degrees and 2 degrees amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

  DOI：

  10.1021/ja2065158

文献信息

• Processes for forming amide bonds and compositions related thereto
  申请人：Liebeskind Lanny S.

  公开号：US08921599B2

  公开（公告）日：2014-12-30

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  该公开涉及生产酰胺键的方法及相关试剂。在某些实施例中，该公开涉及通过混合O-硅烷基硫酸酯和胺在条件下生产酰胺的方法。在另一实施例中，该公开涉及混合硫酸酯、硅基化剂和胺在条件下形成酰胺。