Chiral thioxohydroimidazoles with two sugar moieties. N-, C-, and spiro-nucleosides

Abstract

2-Amino (alkyl and arylamino)-2-deoxy-D-fructose and different sugar isothiocyanates are used in the diastereoselective synthesis of chiral imidazolidine-2-thione N-nucleosides 12-23. Water β-elimination of these compounds produces imidazoline-2-thione N-nucleosides 27-31, whereas cyclodehydration of the same products gives, with high stereoselectivity, chiral spironucleosides with an N-glycosyl radical 34-37. Conformational aspects of some of the prepared compounds are discussed. Copyright (C) 2000 Elsevier Science Ltd.