100313-37-9

Basic information

• Product Name: 1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)carbodiimide
• Synonyms: 1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)carbodiimide
• CAS NO: 100313-37-9
• Molecular Weight: 340.379
• Mol File: 100313-37-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)carbodiimide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)carbodiimide(100313-37-9)
• EPA Substance Registry System: 1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)carbodiimide(100313-37-9)

Safety Data

• Hazardous Substances Data: 100313-37-9(Hazardous Substances Data)

Usage

General Description

1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)carbodiimide is a chemical compound commonly used in peptide synthesis and protein modification. It acts as a coupling reagent, facilitating the formation of amide bonds between amino acids or peptides. The compound contains a carbodiimide functional group, which reacts with carboxylic acids to form an active ester intermediate that can then react with an amine to form the desired amide bond. This process is important in the production of pharmaceuticals, bioconjugates, and other biologically active molecules. Additionally, 1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)carbodiimide is non-toxic and stable, making it a popular choice for chemical reactions in a laboratory setting.

Upstream product

• 100313-33-5 1-(4,4'-dimethoxybenzhydryl)-3-(ethoxycarbonyl)thiourea 
• 19293-62-0 p,p'-dimethoxybenzhydrylamine 

Downstream Products

• 100313-41-5 5-<(4,4'-dimethoxybenzhydryl)amino>-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 

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.