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. 2022 Mar 17;13(14):4122–4130. doi: 10.1039/d2sc00222a

One-pot production of alkyl glycosidesa.

Entry Donor Alcohol Product Isolated yield (%)
1 GlcNAc 2a n-Pentenol graphic file with name d2sc00222a-u2.jpg 73, 48b
2 GlcNAc 2a Benzyl alcohol graphic file with name d2sc00222a-u3.jpg 75
3 GlcNAc 2a Isopropanol graphic file with name d2sc00222a-u4.jpg 76
4 GlcNAc 2a tert-Butanol graphic file with name d2sc00222a-u5.jpg 45
5 GalNAc 2b Benzyl alcohol graphic file with name d2sc00222a-u6.jpg 43
6 ManNAc 2c Benzyl alcohol graphic file with name d2sc00222a-u7.jpg 57
a

Reaction conditions: (i) DMC, Et3N, H2O, 0 °C, 1 h, then freeze-dry; (ii) alcohol as solvent, TsOH (1 equiv.), 4 Å powdered molecular sieves, rt, 3 h.

b

Reaction performed in MeCN/DMF in the presence of 5 equiv. of alcohol as acceptor.