6998-75-0

Basic information

• Product Name: Adenine, 9-(3-deoxy-.beta.-D-threo-pentofuranosyl)-
• CAS NO: 6998-75-0
• Molecular Formula: C₁₀H₁₃N₅O₃
• Molecular Weight: 251.245
• Mol File: 6998-75-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 627.2°Cat760mmHg
• Flash Point: 333.1°C
• Density: 1.91g/cm³
• CAS DataBase Reference: Adenine, 9-(3-deoxy-.beta.-D-threo-pentofuranosyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Adenine, 9-(3-deoxy-.beta.-D-threo-pentofuranosyl)-(6998-75-0)
• EPA Substance Registry System: Adenine, 9-(3-deoxy-.beta.-D-threo-pentofuranosyl)-(6998-75-0)

Safety Data

• Hazardous Substances Data: 6998-75-0(Hazardous Substances Data)

Upstream product

• 40110-98-3 9-(2',3'-O-anhydro-β-D-lyxofuranosyl)adenine 
• 87412-05-3 2'-O-((2,4,6-triisopropylphenyl)sulfonyl)adenosine 
• 127246-65-5 2',3'-di-O-p-tolylsulphonyl-9-β-D-xylofuranosyladenine 

Downstream Products

• 111727-02-7 Trifluoro-methanesulfonic acid (2R,3S,5S)-2-(6-amino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 125542-19-0 9-{(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-fluoro-tetrahydro-furan-2-yl}-9H-purin-6-ylamine 
• 110143-05-0 9-(2,3-dideoxy-2-fluoro-β-D-erythro-pentofuranosyl)adenine 
• 110142-97-7 9-<5-O-(monomethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl>adenine 
• 111727-01-6 6-amino-9-[5-O-(4,4'-dimethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl]-9H-purine 
• 211308-52-0 N-(9-{(2R,3S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide 
• 211308-53-1 Acetic acid (2R,3S,5S)-2-(6-amino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 125944-17-4 N-[9-((2R,3S,5S)-3-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 

Relevant articles and documents

Nucleic acid related compounds. 81. Syntheses of 9-(3-deoxy-β-D-threo- pentofuranosyl)adenine, the core nucleoside of the extraordinarily selective antibiotic agrocin 84, and simplified structural component analogues

Alternative syntheses of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine (4), the core nucleoside of agrocin 84 [and its 2'-deoxy threo isomer 5] were devised: (1) direct conversion of 9-(β-D-arabinofuranosyl)adenine into 9- (2,3-anhydro-β-D-lyxofuranosyl)adenine and regioselective opening of its oxirane ring with sodium borohydride to give 4 and 5 (~7.5:1); (2) treatment of adenosine with sodium hydride and 2,4,6-triisopropylbenzenesulfonyl chloride, and subjection of the resulting 2'(3')-sulfonates to the reductive [1,2]-hydride shift rearrangement with lithium triethylborohydride to give 4 and 5 (~2:1); and (3) subjection of the phenoxythiocarbonyl esters of 9- [2(3),5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]adenine to Barton deoxygenation, and deprotection to give 4 and 2'-deoxyadenosine (~5:1). Methods (2) and (3) gave lower yields. Syntheses of simplified 6-N- and 5'-O-adenosine phosphoramidate model compounds were explored to examine potential access to such features in the structure proposed for agrocin 84.