100313-39-1

Basic information

• Product Name: 5-(3-benzyl-3'-(ethoxycarbonyl)-1-guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide
• Synonyms: 5-(3-benzyl-3'-(ethoxycarbonyl)-1-guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide
• CAS NO: 100313-39-1
• Molecular Weight: 462.462
• Mol File: 100313-39-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-(3-benzyl-3'-(ethoxycarbonyl)-1-guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-benzyl-3'-(ethoxycarbonyl)-1-guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide(100313-39-1)
• EPA Substance Registry System: 5-(3-benzyl-3'-(ethoxycarbonyl)-1-guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide(100313-39-1)

Safety Data

• Hazardous Substances Data: 100313-39-1(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 54035-70-0 ethyl N-(benzylcarbamothioyl)carbamate 

Downstream Products

• 118-00-3 G 

Relevant articles and documents

A New and Efficient Synthesis of Guanosine

New methodology for the preparation of guanosine-type nucleoside analogues from o-amino carbamyl nucleoside precursors has been developed and is demonstrated by the three-step, high-yield synthesis of guanosine (16) from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (1, AICA-riboside).Treatment of 1-(alkoxycarbonyl)-3-(arylmethyl)thioureas 8 with phosgene in the presence of triethylamine affords the highly electrophilic 1-(alkoxycarbonyl)-3-(arylmethyl)carbodiimide reagents 9 in high yield.These reagents are shown to condense with AICA-riboside readily at room temperature to afford N-acyl-N'-(arylmethyl)guanidino-substituted imidazole nucleoside derivatives.One of these derivatives, 5-(N-benzyl-N'-(ethoxycarbonyl)guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (11a), is smoothly debenzylated with cyclohexene in the presence of Pd(0) to afford 5-(N-(ethoxycarbonyl)guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (14).Prolonged heating of 14 in ethanol at reflux affords N-2-(ethoxycarbonyl)guanosine (15) in high yield.The ethoxycarbonyl protecting group of 15 is removed with concentrated NH4OH/pyridine to afford guanosine.This new methodology is much more efficient than those previously reported and should find application for the preparation of a wide variety of guanosine-type nucleoside analogues.