Tetrabutylammonium Fluoride → HCID 59065928, compound

Participants

Reaction Steps

By using an analogous procedure to that described for Example 44, tert-butyl (5S,12S)-12-[(R)-[(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](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (100 mg, 0.097 mmol, obtained from Example 4) and tetrabutylammonium fluoride 0.292 ml, 0.292 mmol) were stirred in tetrahydrofuran (1 ml) under nitrogen for 2.5 hours at room temperature. The residue was chromatographed (flash column, silica gel, 6.5% methanol in methylene chloride) to provide tert-butyl (5S,12S)-12-[(R)-[(3S,4R,5R)-3,4-dihydroxy-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (55 mg, 71%) as a white solid.

Provenance & Evidence