Benzoyl chloride → (6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

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Reaction Steps

1,2-O-Isopropylidene-α-D-xylofuranose (Aldrich, 20 g, 100 mmol) in CH2Cl2 (300 mL) and TEA (44 mL, 310 mmol) was cooled to 0° C. The solution was treated with benzoyl chloride (12.8 mL, 110 mmol) in CH2Cl2 (10 mL) dropwise and stirred for 2 h. The solution was diluted with H2O (30 mL) and washed with saturated NaHCO3 (2×30 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was treated to flash column chromatography (SiO2, 4×20 cm, 0-100% EtOAc-hexanes gradient) to afford compound 9.2 (22.0 g, 71% yield). (Taken from: Johnson, C. R.; Bhumralkar, D. R. Nucleosides & Nucleotides 1995, 14, 185.)

Provenance & Evidence