HCID 69094055, compound → HCID 67509081, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 175 mg of 10% Pd on carbon was added to a solution of benzyl(2-methyl-4-((((2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl)sulfonyl)butan-2-yl)carbamate (700 mg, 1.5 mmol) in 5 mL of methanol. The resultant mixture was degassed and placed under a hydrogen atmosphere, stirring for 3 hours. The suspension was filtered through a pad of celite, washing with methanol, and the filtrate was concentrated under reduced pressure to give ca 496 mg of white foam (quantitative yield). 1H NMR (400 MHz, CD3OD) δ 1.19 (s, 6H), 1.90-1.95 (m, 2H), 3.13-3.18 (dd, J=8.9, 9.9 Hz, 1H), 3.21-3.30 (m, 2H), 3.4-3.43 (m, 3H), 3.48 (s, 3H), 3.61-3.66 (t, J=9.2 Hz, 1H), 4.04-4.10 (m, 1H), 4.69-4.70 (d, J=3.7 Hz, 1H). 13C NMR (100 MHz, MeOD) δ 27.6, 27.7, 34.8, 48.8, 50.8, 53.9, 54.9, 67.3, 71.9, 72.8, 73.3, 100.1. LRMS (ESI/APCI) m/z 328 [M+H]+.

Provenance & Evidence