TRIURETHANE-PROTECTED GUANIDINES AND TRIFLYLDIURETHANE-PROTECTED GUANIDINES - NEW REAGENTS FOR GUANIDINYLATION REACTIONS

New guanidinylation reagents are reported. These reagents consist of N ,N',N ''-tri-Boc-guanidine (1) and N,N',N ''-tri-Cbz-guanidine (2), wh ich allow for the facile conversion of alcohols to substituted guanidi nes. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions,(1) to produce protected alkylated gu anidines. In addition, an extended study of the previously reported re agents(2) N,N'-di-Boc-N ''-triflylguanidine (3) and N,N'-di-Cbz-N ''-t riflylguanidine (4) is presented. The triflyldiurethane-protected guan idine 3 was utilized to guanidinylate primary and secondary amines und er mild conditions with high yield in both solution and on solid phase .