N2 {N2,N6-Bis[3-(2,3,4--tri-O-acetyl-beta-L-fucopyranosylthio)propionyl]-L-lysyl}-N6 [3-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylthio)propionyl]-L-lysine → N2 {N2,N6-Bis[3-(beta-L-fucopyranosylthio)propionyl]-L-lysyl}-N6 [3-(beta-L-fucopyranosylthio)propionyl]-L-lysine

Participants

Reaction Steps

A solution of 25 (500 mg) in methanol-water-triethylamine 5:4:1 (v/v/v, 5 ml) is kept for 3 hours at room temperature and worked-up in the same manner as for 5 to give the title compound (300 mg, 83%): [α]D27 +28.4±0.9° (c 1.0 H2O); NMR (D2O)δ: 4.48 (d, J1,2 =9.5 Hz, 1H, H-1), 4.46 (d, J1,2 =9.5 Hz, 2H, H-1), 4.17, 4.32 (q,q, α-CH), 3.22 (m, ε-CH2), 2.98 (m, SCH2), 2.69 (t, 1H), 2.61 (t, 2H) (SCH2CH2), 1.34-1.90 (m, C-CH2CH2CH2C), 1.25 (d, J=6.0 Hz, CH3 -6).

Provenance & Evidence