Process for production of sugar oxazoline derivatives

A method for production of a sugar oxazoline derivative represented by the following general formula (3), comprising the steps of:

• reacting an acylamino sugar represented by the following general formula (1) with a metal fluoride;
• and
• removing at least a part of a protective group of the resulting sugar oxazoline derivative;
• 9
• wherein X is selected from F, Cl, Br, and I;
• R1 is selected from H and (CH2)n—CH3 wherein n=0 to 5;
• R2, R3, R4, R5, and R6 are each independently selected from H, N3, OH protected by a protective group, NH2 protected by a protective group, and Y—R7 wherein Y is O, NH, or S;
• and
• R7 is a mono- or oligo-saccharide residue, with the proviso that when the residue bears OH, NH2, or COOH, the groups are protected by the protective groups, provided that at least one of R2 and R3 and at least one of R4 and R5 are each H;
• 10
• wherein R1 is the same as that mentioned above,
• R2, R3, R4, R5, and R6 are each independently selected from H, N3, OH which may be protected by a protective group, NH2 which may be protected by a protective group, and Y—R7 Wherein Y is O, NH, or S;
• and R7 is a mono- or oligo-saccharide residue, with the proviso that when the residue bears OH, NH2, or COOH, the groups may be protected by the protective groups, provided that at least one of R2 and R3 and at least one of R4 and R5 are each H.