N-(9-Fluorenylmethoxycarbonyloxy)succinimide → HCID 11814023, compound

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Reaction Steps

A solution of 3-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-L-serine (FIG. 1D) (209.6 mg, 0.82 mmol) and Fmoc N-hydroxysuccinimide ester (9-fluorenylmethyl-N-succinimidyl carbonate) (375.7 mg, 1.63 mmol) in dry pyridine (25 ml) was stirred for 15 h at room temperature. Evaporation and co-evaporation of the reaction mixture with toluene left a syrup which was purified by chromatography on silica gel using dichloromethane-methanol 95:5 as eluent. Pure N-(9-Fluorenylmethyloxycarbonyl)-3-O-(2,3,4-tri-O-acetyl-β-L-fucopyrano syl)-L-serine (294 mg, 88%) was obtained as a white powder, Rf =0.40 (9:1, dichloromethane:methanol). 1H-NMR (CD3OD): ε 7.82-7.25 (m, 8 H, aromatic), 5.18 (m, 1 H, sec. order, H-4), 5.08-4.98 (m, 2 H, sec. order, H-2, 3), 4.50 (d, 1 H, J1,2 =7.5 Hz, H-1), 4.44-3.95 (complex, 6 H, Fmoc-H and serine H's), 3.83 (q, J5,6 =6.25 Hz, H-6), 2.11, 1.99 and 1.92 (each s, 3 H, Ac), 1.10 (d, 3 H, H-6). 13C: ε 102.6 (C-1), 72.5, 71.8 and 70.3 (C-2, 3 and 4), 71.5 and 67.9 (FMOC and serine CH2), 56.5 (serine CHN), 20.8, 20.5 and 20.4 (COCH3), 16.3 (C-6).

Provenance & Evidence