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SYNTHESIS OF 2-ACRYLAMIDOETHYL 3-O-( α- D GLUCOPYRANOSYL-
AND 2-O-ACETYL- α- D -GLUCOPYRANOSYL)- α- D -MANNOPYRANOSIDE
AND ITS CONVERSION INTO ARTIFICIAL ANTIGENS
A. YA. CHERNYAK, I. V. DEMIDOV, N. K. KOCHETKOV
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Synthesis of 2-acrylamidoethyl a-glycosides of 3-O-(α-D -glucopyranosyl)-.D-manno-pyranose and 3-O-(2-O-acetyl-α-D -glucopyranosyl)-D-mannopyranose are described. The key step of the syntheses is glucosydation of 2-benzyloxycarbonylaminoethyl 2,4,6-tri-O-benzyl-α-D-mannopyranoside by 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride according to Igarashi procedure. Use of allyl residue as tho temporary blocking group allowed us to introduce 2-O-acetyl group into the glucose residue. 2-Acrylamidoethyl glucosides prepared were converted into copolymer artificial antigens, which are of interest for studies on immunochemistry of the factor 0:6 of Salmonella O-antigens (serological groups C and H).
Russian Journal of Bioorganic Chemistry 1990, 16 (4):537-549