Ginkgolide B (lb) has been glucosylated in THF with the glucosylidene-derived diazirine 2 under thermal or photochemical conditions. Depending on the amount of 2, we obtained either monoglucosides (5-S), diglucosides (13-17), or triglucosides (21-23). In keeping with earlier results, the use of THF as solvent led mostly to 0-0-glucosides. The modest regioselectivity in the formation of the monoglucosides, glucosylated either at 0-C(l) or 0-C(lO), is rationalized on the basis of the relative kinetic acidity of the intra-and intermolecularly H-bonded OH groups of lb. The tertiary HO-C(3) of the monoglucosides was more readily glucosylated than the secondary HO-C(l) or HO-C(1O) (H-bonded). Glucosidation with 3.5 equiv. of 2 led to triglucosides, with the tri-j-D-glucoside 21 (42%) as the major product. Catalytic hydrogenation afforded the free glucosides 9-12,18-20, and 24.