HCID 446373, compound → HCID 131732355, compound

Participants

Reaction Steps

To a mixture of (2R)-2,3-Bis[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-ol (archaeol) (720 mg; 1.1 mmol), 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (1.4 g; 2.2 mmol) and molecular sieves 4A° (3 g) was added CH2Cl2 (15 ml). After stirring at R.T. under an argon atmosphere for 1 h, triethylsilyltrifluoromethanesulfonate (25 μL; 0.11 mmol) was added and the stirring continued for 40 min. The reaction was quenched with diisopropylethylamine (100 μL). The whole reaction was adsorbed on silica gel and then purified by silica gel chromatography eluting with hexanes:ethyl acetate 9:1 to yield pure product as a viscous oil (0.58 g; 47%) plus some mixed fractions.

Provenance & Evidence