159228-03-2

Basic information

• Product Name: 1-(2-deoxy-5-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine
• CAS NO: 159228-03-2
• Molecular Weight: 426.429
• Mol File: 159228-03-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(2-deoxy-5-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-deoxy-5-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine(159228-03-2)
• EPA Substance Registry System: 1-(2-deoxy-5-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine(159228-03-2)

Safety Data

• Hazardous Substances Data: 159228-03-2(Hazardous Substances Data)

Upstream product

• 35777-72-1 1-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine 
• 874-60-2 4-methyl-benzoyl chloride 
• 50256-07-0 1-[O³,O⁵-bis-(4-methyl-benzoyl)-β-D-erythro-2-deoxy-pentofuranosyl]-6,7-dimethyl-1H-pteridine-2,4-dione 
• 3601-89-6 Hoffer's chlorosugar 
• 5774-32-3 6,7-dimethyllumazine 

Downstream Products

• 159228-04-3 1-(2,3-dideoxy-3-iodo-5-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine 
• 159228-05-4 1-(2,3-dideoxy-5-O-p-toluoyl-β-D-glycero-pentofuranosyl)-6,7-dimethyllumazine 

Relevant articles and documents

Nucleosides. LIV. Synthesis and properties of 3'-azido- and 2',3'-dideoxy- 6,7-diphenyllumazine nucleosides

The best approach for the synthesis of 1-(3-azido-2,3-dideoxy-β-D- erythro-pentofuranosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7- diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy-β-D-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5'-position (17, 34, 49) followed by mesylation at the 3'-OH group and subsequent nucleophilic displacement by lithium azide afforded 19, 29 and 47 which were deprotected by acid treatment to give 3-5 in good yields. The syntheses of 1-(2,3-dideoxy-β-D-glycero- pentofuranosyl)- 6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-β-D-erythro-pentofuranosyl)- 6,7- diphenyllumazine and the corresponding 6,7-dimethyllumazine (26) via their 5'-O-p-toluoyl- (20, 30), and 3'-deoxy-3'-iodo derivatives (24, 31) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV- and NMR spectra.