Butylamine → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-butylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

Participants

Reaction Steps

To a stirred solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (489 mg, 1.26 mmol) in CH2Cl2 (5 mL) was added neat butylamine (197 μL, 2.00 mmol) and the resulting mixture was stirred for 30 min. Saturated aqueous NaHCO3 (20 mL) was added, then the resulting mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were dried (MgSO4) and concentrated. The resulting crude material was purified by flash chromatography on silica gel (hexane(EtOAc 1:1) to give (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-butylthioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white foam (566 mg, 97% yield). 1H NMR (500 MHz, CDCl3) δ 0.94 (t, 3H, J=7.5 Hz), 1.35-1.41 (m, 2H, 1.53-1.59 (m, 2H), 2.06 (s, 3H), 2.08 (s, 3H), 2.10 (s, 3H), 2.14 (s, 3H), 3.38 (br s, 2H), 3.82-3.85 (m, 1H), 4.13-4.16 (m, 2H), 4.20-4.25 (m, 1H), 4.29 (dd, 1H, J=4.5, 12.5 Hz), 5.17-5.22 (m, 2H), 5.73 (d, 1H, J=8.0 Hz), 6.10 (br s, 1H).

Provenance & Evidence