Article abstract of DOI:10.1016/0008-6215(94)80057-X

The synthetic apiosyl-glucosides having (S)-3,7-dimethyl-1,6-octadien-3- yl (linalyl); (R)-1-methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl (terpineyl); (E) and (Z)-3,7-dimethyl-2,6-octadien-1-yl (geranyl and neryl); (S)-3,7- dimethyl-6-octen-1-yl (citronellyl); benzyl and 2-phenylethyl as aglycon moiety were prepared using the stereospecific trichloroacetimidate Schmidt method. The key intermediate diholoside 1,2,3,4-tetra-O-acetyl-6-O-[(3-C- acetoxymethyl)-2,3-di-O-acetyl-β-D-erythrofuranosyl)-β-D-glucopyranose was obtained by Kochetkov glycosylation of a branched-chain tetrofuranose cyanoethylidene derivative. The NMR data (¹H and ¹³C) of the synthetic compounds and the glycosylation shifts of the apiose moiety are reported. The synthetic apiosyl-glucosides having (S)-3,7-dimethyl-1,6-octadien-3-yl (linalyl); (R)-1-methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl (terpineyl); (E) and (Z)-3,7-dimethyl-2,6-octadien-1-yl (geranyl and neryl); (S)-3,7-dimethyl-6-octen-1-yl (citronellyl); benzyl and 2-phenylethyl as aglycon moiety were prepared using the stereospecific trichloroacetimidate Schmidt method. The key intermediate diholoside 1,2,3,4-tetra -O-acetyl-6-O-[ (3-C-acetoxymethyl) -2,3-di-O-acetyl-β-D-erythrofuranosyl)-β-D-glucopyranose was obtained by Kochetkov glycosylation of a branched-chain tetrofuranose cyanoethylidene derivative. The NMR data (¹H and ¹³C) of the synthetic compounds and the glycosylation shifts of the apiose moiety are reported.