N2 {N2,N6-Bis[3-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylthio)propionyl]-L-lysyl}-N6-[3-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)propionyl]-L-lysine → N2 {N2,N6-Bis[3-(beta-D-galactopyranosylthio)propionyl]-L-lysyl}-N6-[3-(beta-D-galactopyranosylthio)propionyl]-L-lysine

Participants

Reaction Steps

A solution of 19 (50 mg) in methanol-water-triethylamine 5:4:1 (v/v/v, 2 ml) was kept for 18 hours at room temperature, and evaporated in vacuo to dryness. The residue was put on a column of silica gel and eluted with chloroform-methanol-water 60:40:10 (v/v/v). The title compound was isolated in 61% yield (20 mg): RF 0.15 (CHCl3 -MeOH-H2O, 60:40:10); NMR (D2O)δ: 4.51 (d, J1,2 =9.5 Hz, 2H, H-1), 4.52 (d, J1,2 =9.5 Hz, 1H, H-1), 4.34, 4.18 (q, q, α-CH), 3.99 (d, J4,3 =3.0 Hz, 3H, H-4), 3.22 (m, εCH2), 3.02 (m, SCH2), 2.70 (t, J=6.5 Hz, 2H, SCH2CH2), 2.62 (t, J=6.5 Hz, 4H, SCH2CH2); [α]D27 -17.3° (c 1.5, H2O).

Provenance & Evidence