HCID 67688225, compound → HCID 67688198, compound

Participants

Reaction Steps

(R)-3,4-Dihydroxy-5-[(Z)-3-octadecenyl]-2(5H)-furanone was prepared as for the S-isomer from (R)-4-hydroxy-5-[(Z)-3-octadecenyl]-3-[(E)-propenyloxy]-2(5H)-furanone in similar yield: mp 65°-67° C.; [α]D25 9.5° (c=0.5 CH3OH); IR (neat, cm-1) 3421 (br), 2917, 2850, 1754, 1666, 734, 719; 1H NMR (CD3COCD3) δ 5.49-5.28 (m, 2H), 4.67 (dd, J=3.4, 7.8 Hz, 1H), 2.32-1.88 (m, 4H), 1.69-1.51 (m, 2H), 1.44-1.25 (m, 24H), 0.87 (t, J=6.7 Hz, 3H); HRMS calculated for C22H38O4 (M+), 366.2770 found 366.2780; analysis calculated for C22H38O4 +0.33 H2O: C, 70.93; H, 10.46: Found: C, 70.53; H, 10.25.

Provenance & Evidence