Reaction Steps
Dissolve (2R,3R)-3-hydroxy-2-(hydroxymethyl)dihydro-2H-pyran-4(3H)-one (662 mg, 4.53 mmol) and DMTCl (1.688 g, 4.98 mmol) in pyridine (5 mL). The reaction was stirred overnight and a TLC was taken in 30% EtOAc/Hexane. The crude reaction mixture was partitioned with 1M CuSO4 (10 mL) and the aqueous layer extracted with DCM (3×30 mL). The combined organic fractions were washed once with water (20 mL) and dried over Na2SO4. The crude product was chromatographed using a gradient from 10%-30% EtOAc/Hexane to yield 1.51 g (74%). 1H NMR (400 MHz, CDCl3) δ 7.49 (dd, J=8.4, 1.2 Hz, 2H), 7.40-7.35 (m, 4H), 7.29 (t, J=4.3, 2H), 7.20 (t, J=7.3 Hz, 1H), 6.86-6.80 (m, 4H), 4.39 (ddd, J=11.3, 7.5, 1.0 Hz, 1H), 4.26 (ddd, J=9.5, 3.8, 1.4 Hz, 1H), 3.79 (s, 6H), 3.70-3.61 (m, 1H), 3.47 (dd, J=5.8, 2.8 Hz, 2H), 3.43-3.34 (m, 2H), 2.90-2.78 (m, 1H), 2.60-2.53 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 208.13, 158.91, 145.38, 136.50, 130.62, 129.60, 128.70, 128.25, 127.20, 113.56, 86.57, 84.09, 74.84, 67.87, 64.25, 55.67, 41.45; IR (neat film) 3458, 2938, 1720, 1509, 1250, 1178, 1110; LRMS for C27H28O6 (M+Na) 471.02.
