Acryloyl‐type polymer fixing 1‐β‐carbonylethyl‐5‐fluorouracil residues through D‐glucofuranoses via ester bonds was synthesized by means of polymerization of the corresponding monomer and polymer reaction. In order to provide the water‐soluble objective polymer, the copolymerization of the acryloyl‐type monomer with acrylamide was carried out. The extent of release of 5‐FU residues from the copolymer was investigated in the enzyme or nonenzyme system in vitro. Furthermore, the antitumor activities of the water‐insoluble homopolymer and water‐soluble copolymer obtained were tested in vivo.

Poly[l -(3-0-[ 1-( 1-carboxyethylaminocarbonyl)ethyl]-6-O-~-glucopyranosyIcarbonyl]ethylene] (3 b) was synthesized as the lipophilic and polymeric model of 4-{N-[2-(2-acetylamino-2-deoxy-3-O-~-glucopyranosyl)propionyl]-~-alanylamino]glutamic acid (1) to the minimum required structure for the immunoadjuvant activity of bacterial cell wall. N-[2-(6-O-acryloyl-l,2-O-isopropylidene-a-~-3-O-g~ucofuranosy~)propiony~]-~-a~a~ne benzyl ester (6) was prepared as a key monomer in the synthesis. The homopolymerization of this monomer was carried out in benzene at 50°C using 2,2'-azoisobutyronitrile as radical initiator to give polymer 7. From the results of copolymerization with styrene, the values of Q and e for the acryloyl type monomer 6 were estimated to be 2,O and O,ll, respectively. The removal of isopropylidene and benzyl protecting groups from homopolymer 7 was carried out by acidic treatment with trifluoroacetic acid/water (vol. ratio 6: 1) and by catalytic hydrogenolysis with palladium carbon in acetone, respectively, to afford the homopolymer 3 b. *) Systematic name: 4-[N-[2-(~-acety~amino-2-deoxy-3-~-~-g~ucopyranosy~)propiony~]-~-a~an-y1amino)glutamic acid.

In order to provide a less toxic 5‐fluorouracil derivative, 1,2:5,6‐di‐O‐isopropylidene‐3‐O‐[3‐(5‐fluorouracill‐yl)‐propionoyl]‐α‐D‐glucofuranose, which was the derivative of 5‐fluorouracil combining indirectly to 3‐position of diacetoneglucose, was synthesized, and its antitumor activity was tested.

1,2:5,6‐Di‐O‐isopropylidene‐3‐O‐[3‐(uracil‐1‐yl)propionoyl]‐α‐D‐glucofuranose and 1,2‐mono‐O‐isopropylidene‐6‐O‐[3‐(uracil‐1‐yl)propionoyl]‐α‐D‐glucofuranose were synthesized.

Die aus D‐Glucose (I) hergestellten Ketale (IIa) und (IIb) werden zu den Acrylestern (III) bzw. (IV) umgesetzt.