(1) Synthesis of Ganglioside Hp-s1 Analogues by Changing Glucosyl to Galactosyl Moiety(2) Synthesis of protected galactosamine

• Main Authors: Chun-Hong Yeh, 葉俊鴻
• Other Authors: Shun-Yuan Luo
• Format: Others
• Language: zh-TW
• Published: 2015
• Online Access: http://ndltd.ncl.edu.tw/handle/32973114632437559919

碩士 === 國立中興大學 === 化學系所 === 103 === 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.