PRODUCTION OF REGULAR GRYCOPEPTIDES

摘要

PROBLEM TO BE SOLVED: To readily produce a glycopeptide useful as a raw material monomer for the subject peptides by carrying out a specific treatment of a fluorinated glycoside of a monosaccharide or an oligosaccharide in which hydroxyl groups are protected with specific protecting groups. SOLUTION: A fluorinated glycoside of a monosaccharide or an oligosaccharide represented by formula I [R1 is OR6 (R6 is H or a hydroxyl group-protecting group); R2 and R3 are each OR7 (R7 is H, a saccharide residue or the like); R4 is CH2OR8 (R8 is R7) or CH3; and R5 is H] is coupled with an amino acid or peptides to provide a compound represented by formula II (R7 and R8 are each one amino acid residue or peptide residue; R9 is H or a lower alkyl; R10 is an amino-protecting group; and R11 is a carboxyl-protecting group). The amino group precursor of the resultant compound represented by formula II, as necessary, is then converted into a protected amino group and the prepared compound is hydrogenated and deprotected to produce the objective compound represented by formula III [R1 is OH or a protected amino; R2' and R3' are each OR7' (R7' is hydroxyl group or a saccharide residue); R4' is CH2OR8' (R8' is H or a saccharide residue) or CH3; and R5' is H].