Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-alpha-D-manno- and beta-D-glucopyranosides with thionucleophiles.
Persubstituted derivatives of phenyl and ethyl 2-O-sulfonyl-1-thio-alpha-D-manno- and beta-D-glucopyranosides were synthesized and reacted either with PhSNa or with MeSNa. The phenyl-1-thio compounds afforded the dithio-1,2-cis-axial/equatorial-alpha-D-glucopyranosides or dithio-1,2-cis-equatorial/axial-beta-D-mannopyranosides by means of S(N)2 type of reactions. Starting from the ethyl-1-thio derivatives intramolecular 1,2-thio-migration took place predominantly. In the case of mannosides both nucleophilic reagents facilitate the formation of 1-SPh- or 1-SEt glycals by elimination. The formation of unsubstituted glycal could also be observed from the ethyl-1-thio derivatives, especially by using PhSNa as a nucleophile. The 1,2-dithio-glycosides are glycosyl donors affording 1,2-trans-2-thio-glycosides.
Research Group for Carbohydrates of the Hungarian Academy of Sciences, H-4010 Debrecen, Hungary.
András
A
Lipták
László
L
Lázár
Anikó
A
Borbás
Sándor
S
Antus
D005947:Glucose / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry*; D055601:Organic Chemistry Phenomena; D013457:Sulfur Compounds / Q000737:chemistry*
D013457:Sulfur Compounds; D005947:Glucose; D008358:Mannose