515815-10-8

Basic information

• Product Name: 2'-deoxy-3',5'-di-O-p-toluoyl-4-chloro-7-methyl-1-β-D-ribofuranosyl-1(H)-imidazo[4,5-c]pyridine
• CAS NO: 515815-10-8
• Molecular Weight: 519.985
• Mol File: 515815-10-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2'-deoxy-3',5'-di-O-p-toluoyl-4-chloro-7-methyl-1-β-D-ribofuranosyl-1(H)-imidazo[4,5-c]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-deoxy-3',5'-di-O-p-toluoyl-4-chloro-7-methyl-1-β-D-ribofuranosyl-1(H)-imidazo[4,5-c]pyridine(515815-10-8)
• EPA Substance Registry System: 2'-deoxy-3',5'-di-O-p-toluoyl-4-chloro-7-methyl-1-β-D-ribofuranosyl-1(H)-imidazo[4,5-c]pyridine(515815-10-8)

Safety Data

• Hazardous Substances Data: 515815-10-8(Hazardous Substances Data)

Upstream product

• 18232-91-2 4,5-diamino-6-chloro-3-methylpyridine 
• 18227-66-2 4-nitramino-3-methylpyridine 
• 18227-67-3 4-amino-3-methyl-5-nitropyridine 
• 1074-98-2 3-methyl-4-nitropyridine N-oxide 
• 1990-90-5 4-amino-3-methylpyridine 
• 1003-73-2 3-picoline-N-oxide 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 18232-95-6 4-chloro-7-methyl-1(H)-imidazo[4,5-c]pyridine 

Relevant articles and documents

The synthesis of anti-fixed 3-methyl-3-deaza-2′-deoxyadenosine and other 3h-imidazo[4,5-c]pyridine analogs

Rotation of a heterocyclic base around a glycosidic bond allows the formation of syn and anti conformations in nucleosides. The syn conformation has been observed primarily in purine-purine mismatches in DNA duplexes. Such mismatches give rise to false positive oligonucleotide hybridization in DNA-based diagnostics. Here we describe the synthesis of an analog of 2′-deoxyadenosine that retains its Watson-Crick functional groups, but cannot form the syn conformation. In this analog, the N3 atom of 2′-deoxyadenosine is replaced by a C-CH3 group to give 7-methyl-1-β-D-deoxyribofuranosyl-1H-imidazo[4,5-c]pyridin-4-ylamine or 3-methyl-3-deaza-2′-deoxyadenosine (3mddA). This modification sterically prevents the syn conformation and 3mddA becomes an anti-fixed nucleoside analog of 2′-deoxyadenosine. The synthesis and conformational analysis of 3mddA and several analogs with an 3H-imidazo[4,5-c]pyridine skeleton are described, as well as their potential applications.