Patent ID: 8835614

Claim:
A method of preparing a compound having the Formula VII: wherein: R 1 is chosen from hydrogen, hydroxyl, optionally substituted lower alkyl, phosphate, sulfate, —OR 7 , a protecting group, and a saccharide; R 2 , R 3 , R 4 , and R 5 are each independently chosen from hydrogen, sulfate, hydroxyl, —OR 8 , a protecting group and a saccharide; R 6 is an alkoxycarbonyl; R 7 and R 8 are each independently chosen from acetyl and optionally substituted lower alkyl; and n is an integer from 2 to 4; comprising: a) treating a compound having the Formula VIII: wherein: R 1 through R 5 are as defined above; and R 9 and R 10 are chosen from hydrogen and hydroxyl, such that when one of R 9 and R 10 is hydroxyl, the other is hydrogen; with a compound having the Formula R 11 R 12 (Sn═O) to form a compound having the Formula IX: wherein: R 1 through R 5 are as defined above; and R 11 and R 12 are each independently chosen from unsubstituted alkyl, or R 11 and R 12 , taken together, are chosen from unsubstituted alkylene; and b) treating the compound of Formula IX, optionally in the presence of a metal fluoride, with a compound having the Formula R 6 —(CH 2 ) n -L, wherein: R 6 and n are as defined above; and L is a halogen; to form the compound of Formula VII.