反应详情

温度

60 °C

To a solution of ((1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′-trihydroxy-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-6′-yl)methyl 4-methylbenzenesulfonate (38 mg, 0.066 mmol) in 1 mL of DMF was added sodium azide (22 mg, 0.338 mmol) and a catalytic amount of TBAI. The solution was warmed to 60° C. and kept at the same temperature overnight. 5 mL of water was added and the solution was extracted with ethyl acetate. The combined organic layers were washed with brine prior to drying over sodium sulfate. Concentration under reduced pressure provided the crude product, which was purified by preparative TLC to give 23 mg of title compound. 1H NMR (CD3OD, 400 MHz) δ 7.36 (s, 1H), 7.22 (s, 1H), 7.08 (s, 4H), 5.14 (d, J=12.4 Hz, 1H), 5.09 (d, J=12.4 Hz, 1H), 4.08 (s, 2H), 3.96-3.91 (m, 1H), 3.77-3.70 (m, 2H), 3.52-3.45 (m, 2H), 3.35-3.31 (m, 1H), 2.59 (q, J=7.6 Hz, 2H), 1.20 (t, J=7.6 Hz, 3H); MS ESI (m/z) 446 (M+1)+, calc. 445.

1. customkept at the same temperature overnight
2. extractionthe solution was extracted with ethyl acetate
3. washThe combined organic layers were washed with brine
4. dry with materialto drying over sodium sulfate
5. concentrationConcentration under reduced pressure
6. customprovided the crude product, which
7. customwas purified by preparative TLC