Dimethylformamide → 2-(10-Methoxycarbonyldecylthio)ethyl 2,3,6-tri-O-acetyl-4-O-{2,3,6-tri-O-acetyl-4-O-[2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-alpha-D-glucopyranosyl]-alpha-D-glucopyranosyl}-beta-D-glucopyranoside

Participants

Reaction Steps

Compound 93 (431 mg, 0.33 mmol), methyl 11-mercaptoundecanoate (105, 114 mg, 0.49 mmol), cesium carbonate (128 mg, 0.39 mmol) and N,N-dimethylformamide (3 ml) were stirred at room temperature for 15 h. The mixture was diluted with dichloromethane, washed with water (neutralization with Duolite H+ resin facilitated the phase separation), and dried (Na2SO4). The solvent was removed and the residue was chromatographed (SiO2, ethyl acetate:isooctane 2:1) to give 95 (243 mg, 50%). [α]D24 +91° (c 4.4, chloroform). 1H-NMR (CDCl3, Me4Si) δ 5.36, 5.28, 5.19 (3d, each 1H, J=3.8, 4.1 and 3.6 Hz, H1', H1", H1"'), 4.57 (d, 1H, J=7.9 Hz, H1), 3.67 (s, 3H, MeO), 2.68, 2.52, 2.31 (3 t, each 2H, J=7 Hz, CH2 --S--CH2 and CH2CO). 13C-NMR (CDCl3, Me4Si) δ 174.1, 170.4-169.1, 100.1 (Cl), 95.6, 95.5, 95.1 (Cl', Cl", Cl"'), 75.0, 73.6, 72.5, 71.9, 71.5, 70.5, 70.2, 69.9, 69.7, 69.6, 69.2, 69.1, 69.1, 69.1, 68.7, 68.3, 67.2, 65.1, 62.9, 62.8, 61.6, 51.2, 33.9, 32.3, 31.1, 29.5, 29.2, 29.1, 29.0, 29.0, 28.9, 28.6, 24.7, 20.7-20.4.

Provenance & Evidence