HCID 86741642, compound → HCID 54300994, compound

Participants

Reaction Steps

A solution of 67 (440 mg, 0.46 mmol) in methanolic sodium methoxide (0.005M, 40 ml) was left at room temperature for 18 h, then neutralized with Duolite C26 (H+) resin and the solvent was removed. The residue was dissolved in water and lyophilized to give 68 (245 mg, 100%) with [α]D21 +71° (c 0.5, water) 1H-NMR (DMSO-d6, 50°, D2O added, Me4Si) δ 4.81 (d, 1H, J=3.5 Hz, H1"), 4.28, 4.20 (d, each 1H, J=7 and 8 Hz, H1 and H1'), 1.14 (t, 3H, J=7 Hz, CH3 --CH2). 13C-NMR (D2O, TSP) δ 106.1, 104.5, 103.2 (Cl, l', l"), 81.5, 80.2, 78.3, 77.7, 77.3, 75.8, 75.0, 73.7, 73.6, 72.0, 71.8, 71.4, 69.1 (CH2), 63.3 (CH2), 63.2 (CH2), 62.9 (CH2), 17.1. Sugar49 and methylation50 analysis was in agreement with the proposed structure.

Provenance & Evidence