SYNTHESIS OF ORGANOPHOSPHORUS DERIVATIVES OF 2-AMINOGLUCOPYRANOSE ANDTHEIR ANTITUMOR ACTIVITIES

A series of novel N-[(p-substituted phenyl) dialkoxyphosphoryl]methyl- 2-amino-2-deoxy-1, 3, 4, 6-tetra-O-acetyl-beta-D-glucopyranose 4 were synthesized by the addition reaction of the imines 3 with the phosphit es. And through subsequent alcoholysis of compounds 4, new 2-aminogluc opyranose derivatives 5 were obtained. H-1 NMR and P-31 NMR spectra in dicated that compounds 4 were mixtures of diastereoisomers. Two isomer s, 4d' and 4i', were isolated and purified by recrystallization, respe ctively. The molecular structure of the isomer 4i' Has determined by X -ray diffraction: Preliminary biological tests showed that some of the se compounds possess inhibiting activities against L(1) (210) and HL-6 0 cells in vitro and S-180 cancer in vivo.