Tetrahydrofuran → HCID 69082734, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Ph3PCH2OCH3Br (2.0 g, 5.90 mmol) in THF (30 mL) was treated with t-BuOK (645 mg, 5.76 mmol) at −10° C. for 30 min, and followed by addition of (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-5-carbaldehyde (700 mg, 1.37 mmol). After stirred for 3 h at 0° C., the resulting solution was quenched with ice-water (20 mL), and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by a silica gel column, eluted with 10-50% ethyl acetate in petroleum ether to give the product 37 as a yellow oil (100 mg, 14%). (ES, m/z) [M+H]+ 515.0; 1H NMR (300 MHz, CDCl3) δ 7.15-7.35 (m, 4H), 6.84-6.98 (m, 4H), 6.45 (d, J=7.8 Hz, 1H), 6.28 (d, J=6.3 Hz, 1H), 5.21 (m, 1H), 4.45-4.89 (m, 4H), 4.18 (t, J=5.7 Hz, 1H), 3.94 (t, J=4.8 Hz, 1H), 3.87-3.91 (m, 1H), 3.78 (s, 6H), 3.56-3.65 (m, 1H), 3.52 (s, 3H), 2.92 (s, 6H).

Provenance & Evidence