SYNTHESIS AND TRANSFORMATIONS OF 2-DEOXY-2-IODO-PYRANOSYL ISOTHIOCYANATES FROM GLYCALS

Authors
SANTOYOGONZALEZ F GARCIACALVOFLORES F ISACGARCIA J HERNANDEZMATEO F GARCIAMENDOZA P ROBLESDIAZ R
Citation
F. Santoyogonzalez et al., SYNTHESIS AND TRANSFORMATIONS OF 2-DEOXY-2-IODO-PYRANOSYL ISOTHIOCYANATES FROM GLYCALS, Tetrahedron, 50(9), 1994, pp. 2877-2894
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
9
Year of publication
1994
Pages
2877 - 2894
Database
ISI
SICI code
0040-4020(1994)50:9<2877:SATO2I>2.0.ZU;2-9
Abstract
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.