Stereospecific synthesis of -anomeric pyrimidine nucleoside

Pyrimidine nucleoside transformations via anhydronucleosides.

The field of nucleosides has undergone rapid growth and development during the past decade'—3. Whereas, earlier studies were concerned with the development of methods for the synthesis of the nucleoside components of the nucleic acids, today several methods are available—each of which has its advantages and limitations. The host of "fraudulent" or "anomalous" nucleosides available today attests...

Stereospecific synthesis of amphetamines

Regioselective addition of aryl lithium to commercially available (S)-(+)-propylene oxide provides the corresponding (S)-aryl-2-propanol. The (R)-amphetamine is obtained by conversion of the alcohol to the tosylate followed by azide displacement and hydrogenation. Mitsunobu conversion of the alcohol to the (R)-bromide followed by azide displacement and hydrogenation affords the (S)-amphetamine....

Anomeric Hydroperoxides; Synthesis, Enantioselective Epoxidation

Some time ago we reported the oxidation of 2,3-unsaturated hexopyranosides and 2-Cmethylene glycosides with hydrogen peroxide in the presence of molybdenum trioxide catalyst to give the corresponding anomeric hydroperoxides 1-5. Relatively stable hydroperoxides 1-5 were used for enantioselective oxidation of prochiral alcohols and sulfides in the presence of Ti(OiPr)4 with stereoselectivities v...

Solution-Phase Parallel Synthesis of Acyclic Nucleoside Libraries of Purine, Pyrimidine, and Triazole Acetamides

Molecular diversity plays a pivotal role in modern drug discovery against phenotypic or enzyme-based targets using high throughput screening technology. Under the auspices of the Pilot Scale Library Program of the NIH Roadmap Initiative, we produced and report herein a diverse library of 181 purine, pyrimidine, and 1,2,4-triazole-N-acetamide analogues which were prepared in a parallel high thro...

Chemical Synthesis of Nucleoside Analogues Chemical Synthesis of Nucleoside Analogues