[Synthesis of 6-O-beta-D-apiofuranosyl-beta-D-glucopyranosides of monoterpenyls]

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-beta-D- erythrofuranosyl)-beta-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.