Water → 4-(2,3,4,6-Tetra-O-acetyl-D-glucopyranosyloxy)-(E)-2-styryl-1,3-dioxolane

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Reaction Steps

4-(2,3,4,6-Tetra-O-acetyl-D-glucopyranosyloxy)benzaldehyde 2 (3.4 g, 7.5 mmol) was dissolved in THF (75 mL), potassium tert-butoxide (0.84 g, 7.5 mmol) and (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide 3 (3.95 g, 9.2 mmol) was added portionwise. The reaction mixture was heated to reflux for 10 h. After completion of the reaction, the mixture was added water and extracted with CH2Cl2 (2×100 mL). Organic layers were combined, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to yield 4 (2.5 g, 64%) as a white powder.

Provenance & Evidence