| 主权项 |
1. A method of preparing an oligosaccharide comprising a linker comprising an aminooxy group, the method comprising:
a) treating a compound having the Formula VIII:wherein:
R1 is selected from the group consisting of hydrogen, hydroxyl, optionally substituted lower alkyl, phosphate, sulfate, —OR7, and a protecting group; R2, R3, R4, and R5 are each independently selected from the group consisting of hydrogen, sulfate, hydroxyl, —OR8, and a protecting group; R7 and R8 are each independently selected from the group consisting of acetyl and optionally substituted lower alkyl; and R9 and R10 are selected from the group consisting of hydrogen and hydroxyl, such that when one of R9 and R10 is hydroxyl, the other is hydrogen; with a compound having the Formula R11R12(Sn═O) to form a compound having the Formula IX:wherein:
R1 is selected from the group consisting of hydrogen, hydroxyl, optionally substituted lower alkyl, phosphate, sulfate, —OR7, and a protecting group; R2, R3, R4, and R5 are each independently selected from the group consisting of hydrogen, sulfate, hydroxyl, —OR8, and a protecting group; R7 and R8 are each independently selected from the group consisting of acetyl and optionally substituted lower alkyl; and R11 and R12 are each independently an unsubstituted alkyl, or R11 and R12, taken together, are unsubstituted alkylene; and b) treating the compound of Formula IX, optionally in the presence of a metal halide, with a compound having the Formula R6—(CH2)n-L,wherein:
R6 is selected from the group consisting of hydroxyl, carboxyl, alkoxycarbonyl, amino, amide, alkylamino, aminoalkyl, aminoxy, hydrazide, hydrazine, optionally substituted alkenyl, and optionally substituted C2-C6 alkyl; n is an integer from 1 to 10; and L is a halogen; to form the compound of Formula VII:wherein:
R1 is selected from the group consisting of hydrogen, hydroxyl, optionally substituted lower alkyl, phosphate, sulfate, —OR7, and a protecting group; R2, R3, R4, and R5 are each independently selected from the group consisting of hydrogen, sulfate, hydroxyl, —OR8, and a protecting group; R6 is selected from the group consisting of hydroxyl, carboxyl, alkoxycarbonyl, amino, amide, alkylamino, aminoalkyl, aminoxy, hydrazide, hydrazine, optionally substituted alkenyl, and optionally substituted C2-C6 alkyl; R7 and R8 are each independently selected from the group consisting of acetyl and optionally substituted lower alkyl; and n is an integer from 1 to 10; c) treating the compound of Formula VII with at least one optionally protected monosaccharide to form an oligosaccharide, wherein the monosaccharide is added to any of R1, R2, R3, R4, or R5; and d) attaching a linker comprising an aminooxy group to the oligosaccharide, wherein the linker comprising an aminooxy group is attached to R6. |
