53009-05-5

Basic information

• Product Name: 3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone
• Synonyms: 3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone
• CAS NO: 53009-05-5
• Molecular Weight: 368.386
• Mol File: 53009-05-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone(53009-05-5)
• EPA Substance Registry System: 3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone(53009-05-5)

Safety Data

• Hazardous Substances Data: 53009-05-5(Hazardous Substances Data)

Upstream product

• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 22900-10-3 2-deoxy-D-ribose 
• 218167-11-4 1-(2'-Deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentafuranosyl)-7-nitroindole 
• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 

Downstream Products

• 108-28-1 protoanemonin 

Relevant articles and documents

Efficient chemical synthesis of oligonucleotides containing the 2- deoxyribonolactone site

A highly efficient synthetic method for incorporation of the deoxyribonolactone lesion into oligonucleotides was developed using the photochemical properties of 7-nitroindole.

The 7-nitroindole nucleoside as a photochemical precursor of 2′-deoxyribonolactone: Access to DNA fragments containing this oxidative abasic lesion

On the basis of molecular modeling studies, the 7-nitroindole nucleoside 1 was selected as a suitable photochemical precursor for photochemical generation of the C1′ deoxyribosyl radical under irradiation, which led to 2′-deoxyribonolactone. The nitroindole nucleoside derivatives 1a and 1b were prepared and their conformation was determined by X-ray crystallography and NMR spectroscopy. The photoreaction of these nucleosides gave the corresponding deoxyribonolactone derivatives efficiently, with release of 7-nitrosoindole. This reaction was successfully applied to synthesis of oligonucleotides containing the deoxyribonolactone lesion.