A new method of glycosidation of phenols has been studied. The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3. 7 and 9, in the presence of tin tetrachloride is described. Glycosides 4, 8 and 10 have been isolated in good yields with high 1,2-trans selectivity. The tributyltin phenoxides 2 have been isolated in quantitative yields, starting from phenols 1 and Bu3SnOMe. This simple method starts from the stable peracetylated sugar, an intermediate of easy access.
Glycosides. Part 1. New synthesis of 1.2-trans O-aryl glycosides, via tributyltin phenoxides / F. Clerici, M.L. Gelmi, S. Mottadelli. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 1994:8(1994), pp. 985-988. [10.1039/P19940000985]
Glycosides. Part 1. New synthesis of 1.2-trans O-aryl glycosides, via tributyltin phenoxides
F. ClericiPrimo
;M.L. GelmiSecondo
;
1994
Abstract
A new method of glycosidation of phenols has been studied. The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3. 7 and 9, in the presence of tin tetrachloride is described. Glycosides 4, 8 and 10 have been isolated in good yields with high 1,2-trans selectivity. The tributyltin phenoxides 2 have been isolated in quantitative yields, starting from phenols 1 and Bu3SnOMe. This simple method starts from the stable peracetylated sugar, an intermediate of easy access.
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