HCID 86741641, compound → HCID 54345445, compound

Participants

Reaction Steps

A solution of 65 (1.0 g, 0.81 mmol) in methanolic sodium methoxide (0.003M, 100 ml) was left at room temperature for 24 h and neutralized with Duolite C26 (H+) resin. The solvent was removed and the residue was dissolved in water (300 ml) and lyophilized to give 66 (580 mg, 88%) with [α]D21 +42° (c 0.7, dimethylsulfoxide). 1H-NMR (DMSO-d6, 50°, D2O added, Me4Si) δ 4.81 (d, 1H, J=3.5 Hz, H1"), 4.27, 4.24 (2d, each 1H, J=7 and 8 Hz, H1 and H1'), 2.67, 2.52 (2t, each 2H, J=7.5 Hz, CH2 --S--CH2), 0.86 (t, 3H, J=6.5 Hz, Me). 13C-NMR (CDCl3 --CD3OD 1:5) δ 105.2, 104.1 (2d, J=162 Hz, Cl, Cl'), 102.6 (d, J=172 Hz, Cl"), 81.1, 80.0, 76.3 (3C), 74.6, (2C), 72.9, 72.5, 71.1, 70.9, 70.4, 70.3 (CH2), 62.7 (CH2), 62.0 (CH2), 61.3 (CH2), 33.2-29.7 (CH2), 23.5 (CH2), 14.4 (CH3).

Provenance & Evidence