N-tert-butoxycarbonyl-L-phenylalanine 9-fluorenylmethyl thioester | 1330059-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-tert-butoxycarbonyl-L-phenylalanine 9-fluorenylmethyl thioester
• CAS: 1330059-29-4
• 化学式: C₂₈H₂₉NO₃S
• 分子量: 459.609
• InChiKey: HNUXJDJQOXALOJ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-phenylalanine 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-Phe-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：

  9-芴基甲基硫醇 、 BOC-L-苯丙氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到N-tert-butoxycarbonyl-L-phenylalanine 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。
• Rapid Formation of N-Glycopeptides <i>via</i> Cu(II)-Promoted Glycosylative Ligation
  作者：Ryan Joseph、Frank Brock Dyer、Philip Garner

  DOI：10.1021/ol302961s

  日期：2013.2.15

  Herein Is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed In the presence of unprotected N-terminal and Lys side chain amines; (2) it Is remarkably fast, going to completion in under 30 min; and (3) It produces glycopeptides without attendant aspartimide formation.