Water → (E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-amino-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide

Participants

Reaction Steps

To a stirred solution of (E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide (0.13 g, 0.25 mmol) in THF (2 mL) is added H2O and triphenylphosphine (0.120 g, 0.5 mmol). After 8 h the reaction solution is evaporated under vacuum to give a semisolid residue that is dissolved in CH2Cl2 (10 mL), adsorbed on silica and chromatographed (CH2Cl2/NH3 to 25% CH3OH/CH2Cl2/NH3 gradient) to give 0.106 g (85%) of (E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-amino-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide as a white solid. MS (ESI) 502.1 (M+H)+

Provenance & Evidence