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 .