REACTION OF SUGAR THIOCYANATES WITH GRIGNARD-REAGENTS - NEW SYNTHESISSF THIOGLYCOSIDES

Authors
PAKULSKI Z PIEROZYNSKI D ZAMOJSKI A
Citation
Z. Pakulski et al., REACTION OF SUGAR THIOCYANATES WITH GRIGNARD-REAGENTS - NEW SYNTHESISSF THIOGLYCOSIDES, Tetrahedron, 50(9), 1994, pp. 2975-2992
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
9
Year of publication
1994
Pages
2975 - 2992
Database
ISI
SICI code
0040-4020(1994)50:9<2975:ROSTWG>2.0.ZU;2-5
Abstract
Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40 degrees C with Grignard reagents t o afford the corresponding alkyl or aryl thioglycosides in good yields . Monosaccharide derivatives having the SCN grouping at other position s form under similar conditions thioethers. Axial thiocyanates do nor react. Elevated temperatures induce side reactions leading to mercapta ns.