3.5.6- tri-O-benzoyl

The hypothesis that, in cyclic derivatives, the low contribution of the benzoyl group on 0-2 to the O — N migration might be attributable to its ready elimination as benzamide was rejected on the basis of the results of the ammonolysis of 2,3,5,6-tetra-O-benzoyl-D-gluco-furanose and 3,5,6-tri-O-benzoyl-D-glucofuranose. The former com-... 

The 3,5,6-tri-O-benzoyl derivative 128 of 123 (R = PhCO) has been prepared by treating the 1,2-O-sulfinyl-a-D-glucofuranose derivative 124 with sodium thiocyanate (95TL5347) (Scheme 38). 

Tri-O-benzoyl-a-D-glucofuranose 1,2-sulfite and bis(trimethylsilyl)uracil heated at 120° for 6 h, cooled to 20 methanol added, and the suspension boiled for a few min l-(3,5,6-tri-0-benzoyl-2-0-trimethylsilyl-p-D-glucofuranosyl)uracil (Y 93%), suspended in methanol containing aq. HCl, and stirred for 2 h at 20° l-(3,5,6-tri-0-... 

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