New glycomimetics: anomeric sulfonates, sulfenamides, and sulfonamides

The synthesis of a variety of new 1-thio-D-glucopyranose derivatives oxidized at the sulfur atom is described, including seven 1-C-sulfonic acids, three sulfonate esters, three sulfinate esters, an S,S'-diglycosyl thiolsulfonate and thiolsulfinate, four S-glycosyl sulfenamides, an S-glycosyl sulfinamide, and two S-glycosyl sulfonamides. These compounds possess unusual anomeric functionality that might be resistant or even inhibitory to normal enzymatic carbohydrate processing, and therefore, they may be of future use in studies of enzyme inhibition, structure, mechanism, and function.     

Synthesis of two novel regioisomeric oxospiropyrazole piperidine scaffolds

The synthesis of two unprecedented regioisomeric oxospiropyrazole piperidine scaffolds is detailed. Their potential utility as templates for drug discovery is also exemplified. Chemical stability and solid state conformation were also evaluated.     

New reactions of selenocarboxylates

By treatment with Woollins' reagent in toluene solution, carboxylic acids are converted to selenocarboxylic acids. The latter react in situ to provide new products of acid- or base-promoted substitution, addition, and amidation.     

Synthesis of spirofuranopyrimidine–piperidines

A concise synthesis of spirofuranopyrimidines is described and relies on the addition of isopropyl 4-oxopiperidine-1-carboxylate to a pyrimidine dianion. The diol intermediate formed is subjected to cycloetherification conditions leading to an unprecedented heterocyclic template.     

The synthesis of azabicyclic heterocycles

An efficient approach to a oxa-azabicyclo[3.2.1] derivatives has been achieved via a double-Mannich reaction of N,N-bis(methoxymethyl)-1-phenylethanamine with symmetrical and unsymmetrical ketones.