Methylamine hydrochloride → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-methylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate
반응식
[C:1]([O:4][C@H:5]1[C@H:10]([N:11]=[C:12]=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2].Cl.[CH3:28][NH2:29]>CC#N>[C:1]([O:4][C@H:5]1[C@H:10]([NH:11][C:12]([NH:29][CH3:28])=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2]참가 물질
4
반응물 2
생성물 1
시약·촉매·용매 1
실험 절차
To a stirred solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (0.51 g, 1.32 mmol) (Jochims, J. C. et al, Tetrahedron, 1965, 21(9), 2611-16) in CH3CN, was added neat methylamine hydrochloride (0.18 g, 2.64 mmol). The reaction was stirred at room temperature until complete by TLC (1.5 h). The reaction was washed with a minimal amount of saturated aqueous NaHCO3 (15 mL). The aqueous layer was then extracted three times with DCM, and the organic layers were combined, dried with MgSO4, filtered and concentrated. The concentrated mixture was purified via flash column chromatography on silica gel (EtOAc:hexanes, 1:1), providing (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-methylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate (0.35 g, 62% yield).1H NMR (500 MHz, CDCl3) δ 2.06 (s, 3H), 2.08 (s, 3H), 2.11 (s, 3H), 2.15 (s, 3H), 2.98 (s, 3H), 3.82-3.88 (m, 1H), 4.10-4.16 (m, 2H), 4.28 (dd, 1H, J=4.6, 12.5 Hz), 5.17-5.22 (m, 2H), 5.74 (d, 1H, J=8.1 Hz), 5.92 (s, 1H), 6.21 (s, 1H).