Synthesis and transformation of 2 thiocarbohydrates : a practical approach for functionalization of thiosugars I. Ceric ammonium nitrate (CAN) mediated thiocyanate radical additions to glycals: In this dissertation a facile entry was developed for the synthesis of 2 thiocarbohydrates and their transformations. Initially CAN mediated thiocyanation of carbohydrates was carried out to obtain the basic building blocks (2 thiocyanates) for the entire studies. Subsequently 2 thiocyanates were reduced to the corresponding thiols using appropriate reagents and reaction conditions. The screening of substrates stereochemical outcome and the reaction mechanism are discussed briefly (Scheme I). Scheme I. Synthesis of the 2 thiocyanates II and reductions to 2 thiols III & IV. An interesting mechanism was proposed for the reduction of 2 thiocyanates II to 2 thiols III via formation of a disulfide intermediate. The water soluble free thiols IV were obtained by cleaving the thiocyanate and benzyl groups in a single step. In the subsequent part of studies the synthetic potential of the 2 thiols was successfully expanded by simple synthetic…