84 硫酸化グルクロン酸含有糖脂質の全合成(口頭発表の部)

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Among various cell surface glycolipids which play important roles in numerous biological phenomena, recent investigations have revealed the biomedical potential of acidic glycolipids 1 and 2. These molecules are structurally featured by the presence of a sulfated glucuronic acid residue which has been revealed to be essential as an antigenic determinant. We report here the regio- and stereocontrolled synthesis of penta- and heptaglycosyl ceramide 1 and 2, which is expected to present a valuable probe for the elucidation of the role of these novel glycolipids. The glycan part of target molecules was designed to be constructed from glucuronate, lactosamine and lactose fragments 6, 7 and 8 which, in turn, were synthesized stereo- and/or regioselectively from readily available compounds. Coupling reaction between 7a and 8 was performed by the action of TMSOTf and subsequent manipulation of the product 22 gave 23. On the other hand, slight modification of this sequence including repetitive glycosylation reactions by using 7b afforded hexasaccharide 33. These compounds were reacted with non-reducing end glucuronate synthon 6, under a condition of CuBr_2-AgOTf-Bu_4NBr, and resultant penta- and heptasaccharide 24 and 34 were transformed into glycosyl fluorides. Final coupling with ceramide 5, followed by chemoselective deprotection of the levulinoyl group, sulfation and complete deprotection afforded target glycolipids 1 and 2.
天然有機化合物討論会の論文
1990-09-25

84 硫酸化グルクロン酸含有糖脂質の全合成(口頭発表の部)

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