具神經再生活性之醣ㄞ姜g胺基酯質SJG-1b之建構單元體的合成

SJG-1化合物是從海洋生物刺參（Stichopus japonicus）的體壁部分所分離得到，為一具雙醣的醣ㄞ姜g胺基酯質（ganglioside）化合物。SJG-1的主要成份為唾液酸（N-glycolylneuramic acid, Neu5Gc）、葡萄糖（glucose）、植物神經鞘胺醇（phytosphingosine）與飽和脂肪酸（saturated fatty acid）等四部份。本論文旨在製備唾液酸、葡萄糖與植物神經鞘胺醇等建構單元體（building block），以利SJG-1b的全合成。唾液酸建構單元體Neu-4是以唾液酸為起始物，經酯化反應、過-氧-乙醯化反應、苯硫醣ㄓ狨頂PN-乙醯化反應等四步化學反應製得，總產率為77%。葡萄糖建構單元體Glc-4是以葡萄糖為起始物，經由甲氧基醣ㄓ狨部B一級醇保護反應、劓礞狨頂P一級醇去保護基反應等四步化學反應製成，總產率75%。植物神經鞘胺醇建構單元體Lyx-7是以來蘇糖(lyxose)為起始物，經氧-異亞丙基化反應、Wittig反應、疊氮等官能基轉換反應，共七步反應所獲得。

關鍵字

醣ㄞ姜g胺基酯質；神經再生；合成；醣

並列摘要

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.