[OH:1][CH:2]1[CH2:7][O:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:16][S:17]([O:1][CH:2]1[CH2:3][CH:4]([NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:15])[CH2:5][O:6][CH2:7]1)(=[O:19])=[O:18]A solution of tert-butyl 5-hydroxy-tetrahydro-2H-pyran-3-ylcarbamate (109 mg, 0.5 mmol) and N,N-dimethylpyridin-4-amine (80 mg, 0.65 mmol) in 10 mL of dichloromethane was cooled in an ice bath, methanesulfonyl chloride (0.05 mL, 0.6 mmol) was added drop-wise. The reaction mixture was stirred overnight at room temperature, then was washed with 50 mL of water, organic phase dried with sodium sulfate filtered and concentrated. The residue was purified by column chromatography (silica gel. 200-300 mesh, eluting with ethyl acetate/petroleum ether=1/1) to afford 5-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-3-yl methanesulfonate (100 mg, 67%) as white solid. LCMS: (M+H)+=318; 1H NMR (300 MHz, CDCl3): δ 4.89-4.83 (m, 1H), 3.99-3.62 (m, 5H), 3.06 (s, 3H), 2.26-2.20 (m, 2H), 1.45 (s, 9H).
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