6998-75-0

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE

The reaction of lithium triethylborohydride with the 2',3'-di-O-p-tolylsulphonyl derivatives of 9-β-D-ribofuranosyladenine, 9-β-D-arabinofuranosyladenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied.The reaction of 2',3'-di-O-p-tolylsulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine.This rearrangement reaction was used for the synthesis of 9-(3,5-dideoxy-β-D-threo-pentofuranosyl)adenine in one step from 2',3',5'-tri-O-p-tolylsulphonyladenosine in 58percent yield.The p-tolylsulphonyl group in the 2'-"up" configuration of unprotected adenine nucleosides was preferentially attacked by LiEt3BH giving S-O-bond scission.This was shown by the formation of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine from 2',3'-di-O-p-tolylsulphonyl-9-β-D-arabinofuranosyladenine and by the formation of 9-β-D-lyxofuranosyladenine from 2'-O-p-tolylsulphonyl-9-β-D-lyxofuranosyladenine with LiEt3BH. 9-β-D-Lyxofuranosyladenine was synthesized from 3',5'-di-O-benzoyl-9-β-D-xylofuranosyladenosine in 88percent yield using a triflate displacement reaction.