本論文的主要目的是合成Pk抗原類似物。Pk抗原屬於三醣體結構，本論文採取以乳糖雙醣與半乳糖單醣作醣基化反應得之，乳醣經由一連串保護去保護的過程後，可得4’位置為羥基的受體，由於保護基的影響創造出的受體屬較弱的受體，因此選用半乳糖1號位置為phosphite且以benzyl作為其他羥基之保護基的強予體作醣基化反應，發現在室溫下可得較快的反應速率，且選擇性相當好，新生成之醣苷鍵為α型式，因此即可得所需之Pk抗原類似物；期間為解決起始物的需求，本論文亦發展了新的全乙醯化方法，利用LiClO4與醋酸酐在40℃下進行反應，即可得高產率之產物，本方法只需簡單的workup步驟，所得的產物純度即已高達98%。

The main goal of the thesis is to synthesize Pk antigen analogues. Because the structure of Pk antigen is a trisaccharide, we used a lactose as acceptor and galactose as donor to perform glycosylation and construct the trisaccharide scaffold. Starting from per-acetyl lactose and through the hydroxyl groups protecting and deprotecting manipulation, the 4’-hydroxyl lactose was obtained as an acceptor. Because of the usage of benzoate as protecting group, the nucleophilicity of this acceptor is weak. A strong donor, 1-phosphite-2, 3, 4, 6-benzylgalactose, was prepared and used to couple with lactose acceptor. The glycosylation was achieved at room temperature with excellentα-selectivity and high yield. By this synthetic pathway, Pk antigen analogue was successfully synthesized in gram scale. To prepare large scale of per-acetyl lactose as starting material, we developed a new method to achieve high yield per-O-acetylation by using catalytic amount of LiClO4 and acetic anhydride at 40℃. The desired per-acetyl lactose was obtained by simple workup procedure (95% yield) with 98% purity.

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