216584-23-5

Basic information

• Product Name: N,N’,N’’-tri(benzyloxycarbonyl)guanidine
• Synonyms: N,N’,N’’-tri(benzyloxycarbonyl)guanidine
• CAS NO: 216584-23-5
• Molecular Weight: 461.474
• Mol File: 216584-23-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N,N’,N’’-tri(benzyloxycarbonyl)guanidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N’,N’’-tri(benzyloxycarbonyl)guanidine(216584-23-5)
• EPA Substance Registry System: N,N’,N’’-tri(benzyloxycarbonyl)guanidine(216584-23-5)

Safety Data

• Hazardous Substances Data: 216584-23-5(Hazardous Substances Data)

Upstream product

• 10065-79-9 N,N’-bis(benzyloxycarbonyl)guanidine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 1206532-50-4 N₂-Boc-N₅,N₇,N₇'-tris-Cbz-3-O-benzyl-(3S)-3-hydroxy-L-arginine tert-butyl ester 
• 1206532-42-4 N₂-Boc-N₅,N₇,N₇'-tris-Cbz-3-O-benzyl-(3R)-3-hydroxy-L-arginine tert-butyl ester 

Relevant articles and documents

Orthoamides by selective borohydride reduction of N,N′,N″-triacyl- and N,N′,N″-tri(alkoxycarbonyl)-guanidines

N,N′,N″-Triacylguanidines and N,N′,N″-tri(alkoxycarbonyl)guanidines were prepared and reduced with borohydride salts in a mixture of tetrahydrofuran and acetic acid to give triacyl and tri(alkoxycarbonyl) orthoamides in yields of 40–85%. However, similar

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), which allow for the facile conversion of alcohols to substituted guanidines. 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, to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents N,N'-di-Boc-N''- triflylguanidine (3) and N,N'-di-Cbz-N''-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.