Benzyl glycosides, preparative liquid

Preparation of the 2-deoxy- -glycoside 47 with triphenyltin hydride The thionocarbonate 46 (0.1 mmol) [see Eq. (19)] was diluted with anhydrous toluene and AIBN was added (0.025 mmol as a standard solution in toluene). The reaction mixture was purged with argon and then heated to 110°C for 5 min, after which triphenyltin hydride (0.2 mmol) was added dropwise as a solution in toluene. The reaction mixture was heated for 1 h, cooled, and purified by placing the entire reaction mixture on a 2 x 16-cm column of silica gel. Elution with 85 15 hexanes-ethy acetate afforded 0-(3,4,6-tri-0-benzyl-2-deoxy-(3-D-glucopyranosyl)-(l—>6)-l,2 3,4-di-0-isopropylidene-a-D-galactopyranose 47 [see Eq (19)] in 90% yield and as a clear liquid [a] -45.1° (c 0.57, CHCy. 

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