HCID 67688157, compound → HCID 67688225, compound

Participants

Reaction Steps

(R)-4-Hydroxy-5-[(Z)-3-octadecenyl]-3-[(E)-propenyloxy]-2(5H)-furanone was prepared as for the S-isomer from (R)-3-Allyloxy-4-hydroxy-5-[(Z)-3-octadecenyl]-2(5H)-furanone in similar yield: mp 42°-45° C.; [α]D25 12.8° (c=0.3, CH3OH); IR (neat, cm-1) 3079 (br), 3004, 2919, 1739, 1681, 1658, 738, 721; 1H NMR (CD3COCD3) δ 6.43-6.36 (m, 1H), 5.49-5.31 (m, 2H), 5.05-4.91 (m, 1H), 4.77 (dd., J=3.5, 7.8 Hz, 1H), 2.24-1.62 (m, 6H), 1.51 (dd, J=1.7, 6.9 Hz, 3H), 1.44-1.24 (m, 24H), 0.87 (t, J=6.8 Hz, 3H); HRMS calculated for C25H42O4 (M+) 406.3083, found 406, 3076.

Provenance & Evidence