Stereoselective synthesis of oligo-alpha-(2,8)-sialic acids.
An efficient and elegant synthesis of alpha(2,8)-oligosialosides is described. The 5-N,4-O-carbonyl-protected sialyl donor undergoes alpha-sialylation in CH2Cl2 to give alpha(2,8)- and alpha(2,9)-disialosides in excellent yields. The 5-N,4-O-carbonyl protecting group was effective in improving the reactivity of the C8 hydroxyl groups toward glycosylation. Using the sialyl building block, the synthesis of tetra-alpha(2,8)-sialic acid was accomplished by using a simple glycosidation and deprotection protocol.
Tanaka
Hiroshi
H
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology 2-12-1-S1-35, Oookayama, Meguro, Tokyo 152-8552, Japan. thiroshi@apc.titech.ac.jp
Nishiura
Yuji
Y
Takahashi
Takashi
T
D015394:Molecular Structure; D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D012794:Sialic Acids