F. Santoyogonzalez et al., SYNTHESIS AND TRANSFORMATIONS OF 2-DEOXY-2-IODO-PYRANOSYL ISOTHIOCYANATES FROM GLYCALS, Tetrahedron, 50(9), 1994, pp. 2877-2894
A convenient one-step synthesis of 2-deoxy-2-iodoglycosyl isothiocyana
tes from monosaccharidic and disaccharidic glycals is reported. Treatm
ent of iodoisothiocyanates 7, 11, 13-15 with ammonia gives the corresp
onding 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-one
s 26-28. Reduction of compounds 7, 8, 13-15 by tributyltin hydride yie
lds the corresponding N-(2'-deoxyglycosyDthioureas 21,22,29-31.