HCID 10841777, compound → HCID 10676823, compound

Participants

Reaction Steps

1-O-Hexadecyl-2-O-methyl-sn-glycerol (433.3 mg, 1.3 mmol) prepared as described above, was glucosylated with 2-O-acetyl-3,4,6-tri-O-benzyl-α, β-D-glucopyranosyl trichloroacetimidate (930 mg, 1.4 mmol) to give 1-O-Hexadecyl-2-O-methyl-3-O-(2′-O-acetyl-3′,4′,6′-tri-O-benzyl-β-D-glucopyranosyl)-sn-glycerol in 76% yield (805 mg). [α]D −8.5 deg. 1H-NMR: δ7.32-7.15 (m, 15H, 3PhCH2) 4.99 (dd, 1H, J1′,2a′=2.5 Hz, J1′,2e′−1.0 Hz, H-1′), 3.93 (m, 1H, H-5′), 3.44 (s, 3H, OCH3), 2.15 (ddd, 1H, J2e′,3′=4.7 Hz, J2e′,2a′=11.5 Hz,H-2e′), 1.7 (ddd, 1H, H-2a′, 1.25 (s, 26H, CH2), 0.87 (t, 3H, CH3). 13C-NMR: δ98.05 (C-1′), 79.33, (C-5′), 62.07 (C-6′), 57.94 (OCH3), 37.36 (C-2′), 31.90, 29.64, 29.48, 29.31, 26.06, 22.67 (CH2), 14.06 (CH3).

Provenance & Evidence