Fig. 3: Substrate scope for the stereoselective preparation of glycosyl phosphosaccharides and N-glycosylation[a]. | Nature Communications

Fig. 3: Substrate scope for the stereoselective preparation of glycosyl phosphosaccharides and N-glycosylation[a].

From: Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors

Fig. 3

A Stereoselective synthesis of the glycosyl phosphates and glycosyl phosphosaccharides. B Synthesis of N-glycosides. a Reaction conditions unless otherwise specified: NaOTf (10–50 mol%), ClCH2CH2Cl (2.0 mL), blue LEDs (15 W), argon atmosphere, 2–12 h. b ClCH2CH2Cl (2.0 mL), blue LEDs (15 W), argon atmosphere, 0.5–4 h. Yields of α/β mixtures (α/β mixtures were not separable), and ratios were determined by 31P NMR. c NaSO4Me (30 mol%), blue LEDs (15 W), 1.5–8 h. d blue LEDs (15 W), 100 °C, 10–14 h. e Bis(trimethylsilyl)trifluoroacetamide (BSTFA, 4.0 equiv), ClCH2CH2Cl: CH3CN = 1:1 (1.0 mL: 1.0 mL), argon atmosphere, 0.5 h; then TMSOTf (10 mol%), blue LEDs (15 W), 0.5–2 h, isolated yield.

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