130676-58-3

Upstream product

• 177779-55-4 9-{(2R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one 
• 958-09-8 2'-deoxy-D-adenosine 
• 229326-12-9 2'-deoxyinosine 5'-acetate 
• 890-38-0 deoxyinosine 
• 58-63-9 Inosine 
• 130676-57-2 5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyinosine 
• 177779-54-3 Imidazole-1-carbothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester 
• 93778-57-5 9-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one 
• 890-38-0 2-deoxyinosine 
• 69655-05-6 Dideoxyinosine 
• 108-24-7 acetic anhydride 

Downstream Products

• 389128-17-0 O⁶-benzyl-5'-O-dibenzyloxyphosphoryl-2',3'-dideoxyinosine 
• 389128-15-8 2',3'-dideoxy-O⁶-(2,4,6-triisopropylbenzenesulfonyl)inosine 
• 389128-16-9 O⁶-benzyl-2',3'-dideoxyinosine 
• 69655-05-6 didanosine 

Relevant academic research and scientific papers

Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2'-deoxyinosine: A new chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine

The selective acylation of the hydroxy groups of the nucleosides inosine 1a and 2'-deoxyinosine lb has been achieved in the presence of Candida antarctica and Pseudomonas sp. lipases in organic solvents; starting from the 5'-acetyl derivative of 2'-deoxyinosine, compound 5a, an efficient chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine 1c has been achieved.

Synthesis of haptens for the development of immunoassays for the monitoring of intracellular anti-HIV nucleosides and nucleotides

A series of nine modified dideoxynucleosides and dideoxynucleotides has been synthesized for preparing antigenic conjugates with keyhole lympet haemocyanin in order to produce specific antibodies, and develop immunoassays. Derivatives of ddI, ddA, d4T, 3TC, and the corresponding 5′-O-monophosphates were designed incorporating an amino spacer at the base for conjugation with the proteinic antigenic carrier.

Synthesis and 1H and 13C NMR spectral characteristics of 8-bromo-2′,3′-dideoxyguanosine and 8-bromo-2′,3′-dideoxyinosine

Reaction of 2′,3′-dideoxyguanosine 1a as 5′-O-tert-butyldimethylsilyl derivative 1b and 2′,3′-dideoxyinosine 2a with bromine in acetate buffer conducted in heterogeneous medium afforded 8-bromo-2′,3′-dideoxyguanosine 3a (44% after deprotection) and 8-bromo-2′,3′-dideoxyinosine 4a (12%) respectively. The change of conformational preferences anti → syn on 8-bromo substitution of 2′,3′-dideoxynucleosides is reflected in the 1H and 13C NMR spectra by characteristic shifts of H-2′, H-3′, C-2′ and C-3′ signals.

Prodrugs of 2',3'-dideoxyinosine (DDI): Improved oral bioavailability via hydrophobic esters

Five ester prodrugs of 2'3'-dideoxyinosine (DDI) were synthesized for the purpose of improving oral bioavailability. The prodrugs, acetate (C2-DDI), octanoate (C8-DDI), stearate (C18-DDI), benzoate (Bz-DDI), and hemisuccinate (Suc-DDI) were proved to quantitatively regenerate their parent drug by enzymatic hydrolysis. Though the chemical stability of the prodrugs under acidic conditions was not improved, their solubility in water was significantly decreased by esterification, except for Suc-DDI. Bioavailability was evaluated by oral administration to rats. Two hydrophobic prodrugs (C8-DDI and Bz-DDI) showed higher absolute bioavailability (23.5% and 31.0%, respectively) than did DDI (15.2%), though that of C2-DDI (11.5%) and Suc-DDI (4.5%) was poor.