Water → HCID 68792675, compound

Participants

Reaction Conditions

Reaction Steps

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-2-(2-(3-chloro-4-(4-ethylbenzyl)phenoxy)ethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (18) (19 mg, 0.03 mmol) was azeotropically dried (3×) with toluene, then dissolved in CH2Cl2 (0.4 mL), cooled to 0° C., and treated with BF3—OEt2 (approx 8 drops of a 48% solution). After 24 h, the reaction was concentrated onto celite and chromatographed over SiO2 (ISCO system, 0-40% EtOAc/hexanes) to provide a film (9.6 mg, 53%). 1H NMR (300 MHz, CDCl3) δ ppm: 7.35 (s, 1H), 7.09 (s, 4H), 6.83 (s, 1H), 5.63 (d, J=9.9 Hz, 1H), 5.40 (t, J=9.6 Hz, 1H), 5.18 (t, J=10.2 Hz, 1H), 4.26-4.33 (m, 1H), 4.05-4.20 (m, 4H), 3.95 (s, 2H), 3.93 (m, 2H), 2.60 (q, J=15, 7.5 Hz, 2H), 2.04 (s, 3H), 2.04 (s, 3H), 2.01 (s, 3H), 1.83 (s, 3H), 1.21 (t, J=7.8 Hz, 3H). LC/MS 99.7% (ELSD) tR=2.93 min, calcd for C31H35ClO10: 602.19, found 620.4 (M+H2O)+.

Provenance & Evidence