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. Author manuscript; available in PMC: 2022 Nov 7.
Published in final edited form as: J Am Chem Soc. 2020 Jun 10;142(25):11102–11113. doi: 10.1021/jacs.0c03298

Scheme 6. Photochemical Thioglycosylation with Anomeric Stannanesd.

Scheme 6.

aα:β 10:1. bα-Stannanes were used. c18 (0.150 mmol, 1 equiv), 49 (1.5 equiv), L11 (45 mol %), KF (3 equiv), blue LED (5 W), 1,4-dioxane (3 mL), 120 °C, 48 h, then 2,3,4-tri-O-benzyl-α-d-glucopyranoside 50 (0.100 mmol), NIS (2.0 equiv), AgOTf (10 mol %), CH2Cl2 (5 mL), 23 °C, 10 h. dGeneral reaction conditions: disulfide (0.100 mmol, 1 equiv), anomeric stannanes (1.5 equiv), L11 (45 mol %), KF (3 equiv), blue LED (5 W), 1,4-dioxane (2 mL), 120 °C, 48 h. Unless otherwise specified, only the α anomer was detected. Anomeric selectivities determined by 1H NMR analysis of unpurified reaction mixtures.