細胞表面上的醣共軛物如醣蛋白及醣脂質，在許多生物過程中扮演著重要的角色，多數的醣共軛物其醣鏈非還原端為唾液酸。然而，這些醣體容易被醣水解酶所降解，利用硫原子取代醣苷鍵的氧原子已常用於提升醣苷鍵對於被酵素水解的穩定度。
本論文的目標是合成硫鍵結之α-2,8唾液酸寡醣體及腫瘤相關抗原GD3。在論文中，運用實驗室過去所開發之”anomeric S-alkylation”的概念來建構硫鍵結之唾液酸寡醣體，以唾液酸單醣32作為構築單元，其變旋異構中心硫原子以第三丁基雙硫鍵作為保護基。利用C2-thioloside作為親核性予體與掛有胺基短鏈之親電性受體C8-iodosialoside在鹼性條件下反應，已經成功地得到硫鍵結之α-2,8唾液酸雙醣、四醣及六醣，經過16步，總產率分別為：9.4%、5.7%和4.8%。
此外，此S-alkylation策略已成功地應用在合成 GD3四醣衍生物上，其非還原端的α-2,8唾液酸雙醣中之醣苷鍵以硫鍵結取代。硫鍵結之GD3四醣體則同樣利用anomeric S-alkylation策略，以C-8”位置被碘活化之-2,3-sialylactoside三醣體作為親電性受體進行反應而得到。將GD3四醣衍生物與攜帶蛋白KLH進行結合，其免疫原性結果正在進行分析中。

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