tert-Butyl (2S,3S)-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-2-(dibenzylamino)-3-hydroxy-propanoate → HCID 59065916, compound

Participants

Reaction Steps

tert-Butyl (2S,3S)-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-2-(dibenzylamino)-3-hydroxy-propanoate (850 mg, 0.942 mmole, obtained from Reference Example 4) was hydrogenated using 10% palladium on carbon in methanol (10 ml) under atmospheric pressure. The catalyst was removed and the volatile was removed in vacuo. The residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=95:2:3) to give the recovered starting material (248 mg, 29%) and tert-butyl (2S,3S)-2-amino-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxypropanoate (141 mg, 21%) as a white amorphous solid.

Provenance & Evidence