Propargylamine → (2S,3R,4R,5R,6R)-6-(acetoxymethyl)-3-(3-(prop-2-yn-1-yl)thioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetate
Reaction equation
[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].[CH2:27]([NH2:30])[C:28]#[CH:29]>C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:10]([NH:11][C:12]([NH:30][CH2:27][C:28]#[CH:29])=[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]Participants
4
Procedure
To a solution of (2S,3R,4R,5R,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetate (1.4 g, 3.6 mmol) in DCM (15 mL) at 0° C., was added propargyl amine (0.345 mL, 5.4 mmol) dropwise. After the addition, reaction mixture was stirred at RT for 1 h. DCM layer was washed with satd. NaHCO3, dried over anhydrous Na2SO4 and concentrated. The crude product (2S,3R,4R,5R,6R)-6-(acetoxymethyl)-3-(3-(prop-2-yn-1-yl)thioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetate (1.59 g, 98%) thus obtained was carried forward without further purification.