(Diethylamino)sulfur trifluoride → HCID 69084882, compound

Participants

Reaction Steps

A solution of (R)-1-((3aR,5R,6S,7R,7aR)-2-(dimethylamino)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)ethanol (280 mg, 0.56 mmol) in dichloromethane (10 mL) was treated with DAST (900 mg, 5.59 mmol) at −78° C. for 10 min and at 0° C. for 1 hr. The reaction was quenched by sat. aqueous Na2CO3 solution (30 mL), and extracted with dichloromethane (2×20 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue, which was purified by silica gel column, eluted with 1-2% methanol in dichloromethane to give compound 50 as a yellow syrup (240 mg, 85%). (ES, m/z): [M+H]+ 505.0; 1H NMR (300 MHz, CDCl3) δ 7.22-7.43 (m, 4H), 6.83-6.94 (m, 4H), 6.38-6.50 (m, 1H), 4.58-4.78 (m, 6H), 3.75-3.90 (m, 8H), 3.46-3.50 (m, 1H), 3.05-3.18 (m, 6H), 1.27-1.36 (m, 3H).

Provenance & Evidence