Synthesis and transformations of 2-deoxy-2-iodo-pyranosyl isothiocyanates from glycals

Abstract

A convenient one-step synthesis of 2-deoxy-2-iodoglycosyl isothiocyanates from monosaccharidic and disaccharidic glycals is reported. Treatment of iodoisothiocyanates 7, 11, 13-15 with ammonia gives the corresponding 2-amino-thiazolines 16, 17, 23-25, respectively. Under the same conditions, iodoisothiocyanate 8 affords the iodothiourea 18. 2-Amino-2-thiazolines 23-25 can be readily transformed into thiazolidin-2-ones 26-28. Reduction of compounds 7, 8, 13-15 by tributyltin hydride yields the corresponding N-(2′-deoxyglycosyl)thioureas 21, 22, 29-31. © 1994.