Silyl-equipped 2 was smoothly converted to ketone 2a in 62% isolated yield. Noteworthy, the presence of a trityl group, potentially susceptible to Birch reduction, had no effect on the reaction outcome, and 3 underwent selective oxidation in 70% yield. In addition, substrate 4, with a tosyl group at C6, provided 4a in 55% yield. The methyl ester of glucuronic acid 5, xyloside 6, 2deoxyglucoside 7, and 6-deoxy-glucoside 8 were smoothly oxidized in moderate to good yields. 4,6-Protected monosaccharide 9 was oxidized in merely 95% NMR yield (60% isolated yield). Somewhat to our surprise, the presence of a benzylidene function had no detrimental effect on the reaction outcome, and glucose derivative 10 provided the C3 oxidation product in 60% isolated yield. We previously observed significant acetal cleavage in the photochemical alkylation reaction. Acetal-protected sorbose 11 provided product 11a in a somewhat disappointing 34% yield, and oxidation of unprotected methyl-β-D-glucopyranoside 12 led to a mixture of unidentified products. The acetal derivative 13 did, however, yield the desired product, albeit in an isolated yield of 21%. Hydrogen atom transfer at the anomeric position is most probably a competing reaction in β-glucosides. Oxidation of methyl N-acetyl glucosamine 14 was incomplete, probably due to its low solubility, and to mitigate this restriction, the acetone derivatives 15 and 16 were synthesized. We were pleased to see that for 15 this led to a high 67% yield in the oxidation reaction. A hypothesis to explain the 33% yield yield for 16a is that hydrogen abstraction by the quinuclidine radical cation is hampered by steric hindrance of the bulky isopropyl substituent. The method is not restricted to monosaccharides, as trehalose derivative 17 produced 17a in a rewarding 42% yield in a double oxidation reaction.