229635-18-1

Upstream product

• 108-24-7 acetic anhydride 
• 136884-14-5 (+)-(2R,4R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>dioxolane-4-carboxylic acid 
• 136884-13-4 (-)-(2R,4R,1'S)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-4-(1,2-dihydroxyethyl)dioxolane 
• 546-67-8 lead(IV) tetraacetate 
• 141119-41-7 (+)-(2R,4R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>dioxolane-4-carboxylic acid methyl ester 

Downstream Products

• 145439-99-2 (+)-(2R,4S)-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-6-chloropurine 
• 145439-98-1 (-)-(2R,4R)-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-6-chloropurine 
• 141119-30-4 (+)-(2R,4S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-5-iodouracil 
• 141119-29-1 (+)-(2R,4R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-5-iodouracil 
• 145440-23-9 (-)-(2R,4R)-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-2,6-dichloropurine 
• 141119-28-0 (+)-(2R,4S)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>uracil 
• 141119-27-9 (+)-(2R,4R)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>uracil 
• 141119-24-6 (+)-(2R,4S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-5-fluorouracil 
• 141119-23-5 (+)-(2R,4R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-5-fluorouracil 
• 145440-06-8 (-)-(2R,4R)-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>hypoxanthine 
• 145440-07-9 (+)-(2R,4S)-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>hypoxanthine 
• 145440-09-1 (-)-(2R,4R)-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>adenine 
• 145440-10-4 (+)-(2R,4S)-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>adenine 

Relevant academic research and scientific papers

METHOD FOR THE PRODUCTION OF OH PROTECTED [4-(2.6-DIAMINO-9H-PURINE-9-YL)- 1.3-DIOXOLANE-2-YL]METHANOL DERIVATIVES

The invention relates to a method for the production of OH protected [4-(2,6-diamino-9H-purine-9-yl)-1,3-dioxolane-2- yl]methanol derivatives in a racemically or optically pure form by directly reacting 2.6-diaminopurine and/or a single or multiple silylated 2.6-diaminopurine with a sugar component. An auxiliary agent in the form of a 1.3- dicarbonyl compound or a silylated derivative of a 1.3 dicarbonyl compound is present during the reaction of the glycosylation, in addition to a Lewis acid.

Asymmetric Synthesis of 1,3-Dioxolane-Pyrimidine Nucleosides and Their Anti-HIV Activity

In order to study the structure-activity relationships of dioxolane nucleosides as potential anti-HIV agents, various enantiomerically pure dioxolane-pyrimidine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear cells.The enantiomerically pure key intermediate 8 has been synthesized in nine steps from 1,6-anhydro-D-mannose (1), which was condensed with 5-substituted pyrimidines to obtain various dioxolane-pyrimidine nucleosides.Upon evaluation of these compounds, cytosine derivative 19 was found to exhibit the most potent anti-HIV agent although it is the most toxic.The order of anti-HIV potency was as follows: cytosine (β-isomer) > thymine > cytosine (α-isomer) > 5-chlorouracil > 5-bromouracil > 5-fluorouracil derivatives.Uracil, 5-methylcytosine, and 5-iodouracil derivatives were found to be inactive.Interestingly, α-isomer 20 showed good anti-HIV activity without cytotoxicity.As expected, other α-isomers did not exhibit any significant antiviral activity. (-)-Dioxolane-T was 5-fold less effective against AZT-resistant virus than AZT-sensitive virus.

Asymmetric synthesis of enantiomerically pure (-)-(1'R,4'R)-dioxolane-thymine and its anti-HIV activity

An asymmetric synthesis leading to the enantiomerically pure dioxolane-T has been achieved and its crystal structure has been determined and compared to the previously reported racemate. (-)-(1'R,4'R)-dioxolane-T was found to have potent and selective ant