以D-葡萄糖为原料,通过甲基葡萄糖苷的选择性6-位硅烷化、乙酰化、脱硅烷基保护、三氟甲磺酰化得到甲基6-O-三氟甲磺酰基-2,3,4-O-三乙酰基葡萄糖苷,进一步与亮氨酸甲酯反应得到N-[6-(甲基2,3,4-O-三乙酰基-α-D-吡喃葡萄糖苷)]亮氨酸甲酯,通过红外、核磁共振氢谱、质谱和元素分析对其结构进行了表征.
[1] FEIZI T, BUNDLE D. Synthesis of oligosaccharides, glycolipids and glycopeptides [J]. Current Opinion in Structural Biology 1992, 2.
[2] PAULSEN H. Syntheses, conformations and X-Ray structure analyses of the saccharide chains from the core regions of glycoproteins [J]. Angewandte Chemie International Edition 1990, 29.
[3] VARKI A. Biological roles of oligosaccharides:all of the theories are correct [J]. Glycobiology 1993, 3.
[4] Koeller, KM, Wong, CH. Emerging themes in medicinal glycoscience. [J]. Nature biotechnology 2000, 8(8).
[5] NICOLAOU K C, PAVIA M R, SEITZ S P. Synthesis of 16-membered-ring macrolide antibiotics.4.carbomycin B and leucomycin A3:total synthesis of cyclic key intermediate [J]. Journal of the American Chemical Society 1981, 103.
[6] OGILVIE K K, HAKIMELAHI G H, PROBA Z A. Silylated derivatives of arabinonucleosides [J]. Tetrahedron Letters 1982, 23.
[7] WOLFROM M L, THOMPSON A. Acetylation [M]. New York:Academic Press, Inc 1963.
[8] CORE Y E J, VENKATESWARLU. Protection of hydroxyl groups as tert-butyldi methylsilyl derivatives [J]. Journal of the American Chemical Society 1972, 94.