請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/90618
標題: (1) Synthesis of Ganglioside Hp-s1 Analogues by Changing Glucosyl to Galactosyl Moiety (2) Synthesis of protected galactosamine
(1)將葡萄醣置換成半乳醣之神經節苷脂Hp-s1衍生物之合成 (2)全保護半乳醣胺之合成
作者: 葉俊鴻
Chun-Hong Yeh
關鍵字: Ganglioside Hp-s1
galactosamine
神經節苷脂Hp-s1
半乳醣胺
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摘要: In first part of thesis, synthesis of analogues of ganglioside Hp-s1 varying at central glucosyl moiety is presented. In order to optimize the important role of central glucosyl moiety of ganglioside Hp-s1 in neurology, we have replaced glucosyl moiety to galactosyl sugar unit and synthesized new analogues (2c-2d) including the changes in stereochemistry at C-1 of galactose sugar moiety. In second part of thesis, we have synthesized the intermediate derivative of galactosamine starting from glucosamine hydrogen chloride. We have developed the two one-pot synthesis of fully protected galactosamine. First one-pot method includes, azidation and silylation to afford fully protected azido-TMS compound 121. Second one-pot method includes, C-4 and C-6 benzylidene protection and acetylation provided corresponding benzylidene protected azide 106. Finally, the intermediate derivative of galactosamine was obtained after these two one-pot operation in good overall yields. This intermediate compound of galactosamine is a core unit of Tn antigen, GM1, GD2, GT2. However, using the developed strategy in this thesis, we could use the intermediated compound for the synthesis of various gangliosides such as Tn, antigen, GD2, GT2.
在論文第一部分中,為了尋找更有效的神經醣苷脂Hp-s1,本實驗室合成出中央醣體不同的神經醣苷脂Hp-s1衍生物,本篇嘗試將Hp-s1的中央醣體由葡萄醣更動為半乳醣,並且改變醣鏈結的立體位向選擇,成功的合成出新的Hp-s1衍生物2c及2d。 在論文第二部分中,我們藉由葡萄醣胺鹽酸鹽經過兩次一鍋化反應及開環、翻轉等四步反應可以成功合成出全保護半乳醣胺衍生物。在第一次一鍋化反應中先置換成疊氮及矽烷保護形成化合物121,在以第二次一鍋化反應將C-4、C-6作苯基保護及C-1、C-3的乙醯基保護形成化合物106,在經過兩步反應可得到高產率的半乳醣胺衍生物,並可作為Tn抗原、GM1、GD2、GT2等化合物的合成建構基石。
URI: http://hdl.handle.net/11455/90618
文章公開時間: 2018-06-12
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