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. 2021 Jul 12;1(8):1275–1287. doi: 10.1021/jacsau.1c00201

Scheme 1. Synthesis of 3-Thiopropyl Glycosides G27SH, G30SH, and G28SH.

Scheme 1

TMS-OTf, DCM, 0 °C to rt, 1 h, MS 4 Å (50–67%).

HF·pyridine, THF, 0 °C then rt, 1 h (65–88%).

TFA/H2O/DCM 1:1:10, rt, 15 min (70–90%).

AcSH, AIBN or DPAP, THF, UV light (350 nm), 6-12 h (85–93%).

NaOMe, MeOH, rt, 2 h (quant.).

NIS, AgOTf, DCM, 0 °C to rt, 45 min, MS 4 Å (47%).

HF·pyridine (1.2 equiv), THF, 0 °C, 6 h or HF·pyridine (excess), THF, 0 °C, 2 h (60%).