Triacetoxyperiodinane → HCID 69082386, compound

Participants

Reaction Steps

A solution of 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 (450 mg, 0.90 mmol, mixture of diastereomers, faster eluting isomer: slower eluting isomer 1:5 by HPLC and 1HNMR) in dichloromethane (20 mL) was treated with Dess-Martin reagent (760 mg, 1.80 mmol) for 2 hours at room temperature. The reaction mixture was quenched by sat. aqueous Na2S2O3 solution (20 mL) and sat. aqueous NaHCO3 solution (20 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 2-3% methanol in dichloromethane to give compound 33 as a yellow syrup (400 mg, 88%). (ES, m/z): [M+H]+ 501.0; 1H NMR (300 MHz, CDCl3) δ 7.25-7.30 (m, 4H), 6.83-6.90 (m, 4H), 6.29-6.31 (d, J=6.0 Hz, 1H), 4.26-4.64 (m, 6H), 3.81-3.98 (m, 8H), 2.96-3.02 (m, 6H), 2.17 (s, 3H).

Provenance & Evidence