A facile one-pot synthesis of N-alpha-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics

作者：Sureshbabu Vommina V^*; Vasantha B; Nagendra G

来源：Tetrahedron Letters, 2012, 53(11): 1332-1336.

DOI：10.1016/j.tetlet.2011.12.093

• Oxadiazole-2-thiol
• Peptidomimetics
• Glycosylated amino acids
• Ultrasonication

A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated.

• 出版日期2012-3-14