Mariño-Albernas J, Verez-Bencomo V, Gonzalez-Rodriguez L, Perez-Martinez C S, Gonzalez-Abreu Castell E, Gonzalez-Segredo A
Laboratory for Carbohydrate Chemistry, Facultad de Quimica, Universidad de la Habana, Cuba.
Carbohydr Res. 1988 Dec 1;183(2):175-82. doi: 10.1016/0008-6215(88)84072-2.
The trisaccharide allyl O-(3,4-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl-al pha-L- rhamnopyranosyl)-(1----2)-3-O-methyl-alpha-L-rhamnopyranoside was synthesized from partially methylated monosaccharide derivatives. Condensation of 1,4-di-O-acetyl-2,3-di-O-methyl-alpha-L-rhamnopyranose promoted by boron trifluoride etherate with the appropriate alcohol proceeded stereoselectively and with very high yields. Selective deacetylation and glycosylation with 2,4-di-O-acetyl-3,6-di-O-methyl-alpha-D-glucopyranosyl bromide led to a trisaccharide. The acrylamide copolymers of mono-, di-, and tri-saccharide were compared in their ability to specifically bind antibodies from leprosy patients.
三糖烯丙基 O-(3,4-二-O-甲基-β-D-吡喃葡萄糖基)-(1→4)-O-(2,3-二-O-甲基-α-L-鼠李吡喃糖基)-(1→2)-3-O-甲基-α-L-鼠李吡喃糖苷是由部分甲基化的单糖衍生物合成的。在三氟化硼乙醚的促进下，1,4-二-O-乙酰基-2,3-二-O-甲基-α-L-鼠李吡喃糖与适当的醇进行缩合反应，具有立体选择性且产率很高。用 2,4-二-O-乙酰基-3,6-二-O-甲基-α-D-吡喃葡萄糖基溴进行选择性脱乙酰化和糖基化反应，得到一种三糖。比较了单糖、二糖和三糖的丙烯酰胺共聚物特异性结合麻风病患者抗体的能力。
