Carbohydrate Research p. 79 - 90 (1980)
Update date:2022-08-04
Topics:
Pavia, Andre A.
Rocheville, Jean-Michel
Ung, Sak N.
In the presence of trifluoromethanesulfonic (triflic) anhydride as catalyst and dichloromethane as solvent, in the cold, 2,3,4,6-tetra-O-benzyl-D-glucopyranose, 2,3,4,6-tetra-O-benzyl-D-galactopyranose, and 2,3,4,6-tetra-O-benzyl-D-mannopyranose were converted in almost quantitative yield to a 2:1 mixture of the corresponding α,α-(1->1) and α,β-(1->1) disaccharides.Hence, pure 2,3,4,6,2',3',4',6'-octa-O-benzyl derivatives of α,α-trehalose, and the D-galacto and D-manno analogues were obtained, after column chromatography, in 55-65 percent yield.Hydrogenolysis gave the corresponding free sugars.The pure anomers were obtained in 10-34 percent yield.The potentiality of the method was demonstrated by the synthesis of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 2,3:4,5-di-O-isopropylidene-β-D-fructopyranoside in 50 percent yield, and of N-(benzyloxycarbonyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-threonine methyl ester in 65 percent yield.
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(1979)