HCID 86621845, compound → HCID 25154352, compound

Participants

Reaction Steps

(2′S,3′R,4′S,5′R,6′R)-3′,4′,5′-Tris(benzyloxy)-6′-(benzyloxymethyl)-6-(4-ethylbenzyl)-3′,4′,5′,6′-tetrahydrospiro[chroman-4,2′-pyran] (11) (13.4 mg (0.018 mmol) was dissolved in MeOH (1 mL). Pd/C (5 mg, 10% Pd/C) was added, the reaction vessel was flushed with H2, (3×, alternating with high vacuum), then stirred under an atmosphere of H2. After 3 h, additional Pd/C (5 mg) was added and the vessel flushed again with H2 (3×, alternating with high vacuum), and the reaction mixture was stirred for an additional 16 h. The crude mixture was concentrated onto celite and chromatographed over SiO2 (ISCO system, 0-20% MeOH/CH2Cl2) to provide two fractions, with 1.7 and 6.3 mg respectively. (8 mg total, >100%). The smaller fraction was of the highest purity and was submitted for biological analysis. (The second fraction had slightly dark color, indicating some Pd contamination.) For the pure fraction: 1H NMR (300 MHz, CDCl3) δ ppm: 7.22 (m, 2H), 6.99-7.11 (m, 5H), 6.77 (d, J=8.1 Hz, 1H), 4.27-4.33 (m, 1H), 4.04-4.11 (m, 1H), 3.59-3.97 (m, 6H), 2.60 (q, J=15, 7.5 Hz, 2H), 2.37-2.46 (m, 1H), 2.12 (m, 1H), 1.21 (t, J=7.5 Hz, 3H). LC/MS 98.4% (ELSD) tR=1.80 min, calcd for C23H28O6: 400.19, found 423.0 (M+Na)+.

Provenance & Evidence