Abstract
The compound SJG-1, which was isolated from the body wall of the sea cucumber Stichopus japonicus, is a ganglioside containing disaccharides. The compound is composed of N-glycolylneuraminic acid (Neu5Gc), glucose, phytosphingoside and fatty acid. The synthesis of SJG-1b and the building blocks of SJG-1b, such as N-glycolylneuramic acid (Neu5Gc), glucose, phytosphingosine and saturated fatty acid are discussed in this thesis. The building unit, Neu-4, is formed by the sialic acid through the esterification, per-O-acetylation, thiophenol glycolsylation and N-acetylation in 75% total yield is for four-step procedure. The glucose building unit, Glc-4, is prepared form glucose through the methyl glycolsylation, protection of primary alcohol, benzylation and deprotection primary alcohol, and the method requires four steps to give the product, Glc-4, in 75% total yield. The building unit of phytosphingosine, Lyx-7, is made from lyxose, while undergoed O-isopropylidene reaction, Wittig reaction, azidization and functional group transformation total for seven steps.
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