180403-67-2

Upstream product

• 18055-46-4 N-trimethylsilanyl-N-(7-trimethylsilanyl-7H-purin-6-yl)-benzamide 
• 180403-66-1 Benzoic acid (2S,3R,4R,5S)-4,5-diacetoxy-3-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester 
• 4005-49-6 N-benzoyladenine 
• 69832-48-0 ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 
• 180403-65-0 Benzoic acid (3aR,5S,6R,6aR)-6-methanesulfonyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 180403-62-7 3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methanesulfonyloxymethyl-α-D-allofuranose 
• 180403-63-8 Methanesulfonic acid (3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ylmethyl ester 
• 180403-64-9 Methanesulfonic acid (3aR,5S,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ylmethyl ester 
• 98-88-4 benzoyl chloride 

Downstream Products

• 180403-73-0 Benzoic acid (2S,3R,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester 
• 180403-72-9 Benzoic acid (2S,3S,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester 
• 180403-71-8 Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester 
• 244611-81-2 Benzoic acid (2S,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-3-(diisopropoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester 
• 244611-85-6 Benzoic acid (2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(diisopropoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester 
• 180403-69-4 Benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester 

Relevant academic research and scientific papers

Studies on the phosphonate isostere of nucleoside 3'- and 2'-phosphates as precursors of the related oligonucleotides

Synthesis of 2',3'-dideoxy-3'-C-(dihydroxyphosphinylmethyl)-adenosine and -thymidine 5, as well as of 2'-deoxy-2'-C-(dihydroxyphosphinylmethyl)- adenosine and -thymidine 9 was accomplished with the use of the universal carbohydrate precursor 3-deoxy-1,2;5,6-di-O-isopropylidene-3-C- (mesyloxymethyl)-α-D-allofuranose (1).

Synthesis and antiviral activity of 3'-C-branched-3'-deoxy analogues of adenosine

The synthesis of some 3'-C-branched-3'-deoxy adenine nucleosides is described. Starting from the known 3-deoxy-3-C-(hydroxymethyl)-1,2;5,6-di-O- isopropylidene-α-D-allofuranose (1), a versatile glycosylating agent, namely 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-(mesyloxymethyl)-β-D-ribofuranose (6), was prepared in three steps. Condensation of the latter with bis(trimethysilylated) N6-benzoyladenine in the presence of tin(IV) chloride gave the N9-β-nucleoside 7. Compound 7 was converted into (i) 9-[3-C- (azidomethyl)-3-deoxy-β-D-ribofuranosyl]adenine (10), (ii) 9-[3-C- (azidomethyl)-3-dideoxy-β-D-glycero-pent-2-enofuranosyl]adenine (14) and 9- [2-azido-3-C-(azidomethyl)-2,3-dideoxy-β-D-arabinofuranosyl]adenine (15), and (iii) 9-[3-deoxy-2-O,3-C-(methylene)-β-D-ribofuranosyl]adenine (16). None of the tested nucleosides showed marked cytostatic or antiviral activity in vitro.