Y. Suman Reddy

Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones

Azidation of 1,2-anhydro sugars with NaN(3) in CH(3)CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.

Acetyl chloride-silver nitrate-acetonitrile: a reagent system for the synthesis of 2-nitroglycals and 2-nitro-1-acetamido sugars from glycals.

A new reagent system comprising acetyl chloride, silver nitrate, and acetonitrile has been developed for the synthesis of 2-nitroglycals from the corresponding glycals. Under certain conditions, the formation of 2-nitro-1-acetamido sugars has also been observed. In addition, a few other non-carbohydrate-derived olefins also gave the corrresponding conjugated nitroolefins.

Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors

Synthesis of polyhydroxylated oxabicyclo[4,4,0]decanes, which constitute a new family of annulated carbasugars, has been accomplished in a stereoselective manner by employing readily available 1,2-anhydro-3,4,6-tri-O-benzyl-alpha-d-glycopyranoses.

Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside.

Summary A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected glycals and by employing several nucleophiles. The obtained C-allyl glycoside has been utilized for the synthesis of a orthogonally protected 2-amino-2-deoxy-C-glycoside.

Synthesis of unnatural indolizidines, pyrrolizidine and C-alkyl iminosugars from sugar derived hemiaminals

Novel biologically important mono- and bicyclic iminosugars have been synthesized from commercially available sugars following high yielding and short synthetic sequences. These unnatural N-heterocycles have been further tested against several glycosidases and some of them showed good inhibition of the enzymes with moderate selectivity.