Methanol → 2'-Deoxy-2'-(N-Fmoc-beta-alanineamido)uridine

Participants

Reaction Steps

Referring to FIG. 10, EEDQ (4.2 g, 17 mmol) was added to the solution of 2′-amino-2′-deoxy uridine (4 g, 16.45 mmol) and N-FMOC-beta-alanine (5.1 g, 16.45 mmol) in methanol and the reaction mixture was boiled for two hours. Subsequent flash chromatography on silica using a linear gradient of methanol (5% to 10% ) in dichloromethane afforded 6 g of 2′-Deoxy-2′-(N-Fmoc-beta-alanineamido) uridine (77%). 1H NMR (CDCl3-DMSO-d6) d 10.398 (s, 1H, N3-H), 6.98-7.63 (m, H6, Fmoc), 6.16 (t, 1H, NHFmoc), 5.73 (d, 1H, H1′, J1′,2′ 8.4), 5.34 (d, 1H, H5), 4.22 (m, 1H, 2′-H) 3.98 (dd 2H, CH2), 3.88 (m, 1H, 3′-H), 3.77 (br s, 1H, 4′-H), 3.43 (m, 2H, 5′-CH2), 3.1 (m, 2H, CH2NHFmoc), 2.07 (t, 2H, CH2CO).

Provenance & Evidence