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

Participants

Reaction Steps

A solution of 15 (52 mg, 0.025 mmol) in methanol-water-triethylamine 5:4:1 (v/v/v, 1 ml) is kept for 3 hours at room temperature, and evaporated in vacuo to a residue that is put on a Sephadex G-15 column and eluted with water. Fractions 1-4 (12 ml), eluted after blue dextran, are collected and lyophilized to give 16 (25.1 mg, 71%): [α]D27 +96.2° (c 1.0, H2O); NMR (D2O)δ: 5.37 (s, 1H, H-1), 5.34 (s, 3H, H-1) 4.34 (2H), 4.18 (1H) (α-CH), 3.22 (m, ε-CH2), 2.93 (m, SCH2), 2.70 (t, 2H), 2.60 (t, 6H) (SCH2CH2), 1.34-1.94 (CCH2CH2CH2C).

Provenance & Evidence