SYNTHESIS OF BLOOD-GROUP SUBSTANCES .12. SYNTHESIS OF THE TETRASACCHARIDE O-ALPHA-L-FUCOPYRANOSYL-(1-]2)-[O-ALPHA-D-GALACTOPYRANOSYL-(1-]3)]-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE, THE ANTIGENIC DETERMINANT OF HUMAN BLOOD-GROUP-B (TYPE-2)
SYNTHESIS OF BLOOD-GROUP SUBSTANCES .12. SYNTHESIS OF THE TETRASACCHARIDE O-ALPHA-L-FUCOPYRANOSYL-(1-]2)-[O-ALPHA-D-GALACTOPYRANOSYL-(1-]3)]-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE, THE ANTIGENIC DETERMINANT OF HUMAN BLOOD-GROUP-B (TYPE-2)
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DOI：
10.1016/s0008-6215(00)80391-2
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发表时间：
1981-01-01
影响因子：
3.1
通讯作者：
SINAY, P
中科院分区：
文献类型：
--
作者：
MILAT, ML;SINAY, P
在氯化锌存在下，用苯甲醛与苯甲醛反应，然后进行区域选择性苯甲酰化反应(二氯甲烷中的N-苯甲基咪唑)，得到结晶的苄基2-acetamido-3，6-di-O-benzyl-2-deoxy-4-O-.beta.-D-galactopyranosyl-.alpha.-D-glucopyranoside该二糖在对甲苯磺酸和分子筛4的存在下，与2，3，4-tri-O-benzyl-1-O-(N-methylacetimidyl)-.beta.-L-fucopyranose在硝基甲烷中缩合，得到苯基O-(2，3，4-tri-O-benzyl-.alpha.-L-fucopyranosyl)-(1.fwdarw.2)-O-(3-O-benzyl-4，6-O-benzylidene-.beta.-D-galactopyranosyl)-(1.fwdarw.4)-2-acetamido-3，6-di-O-benzyl-2-deoxy-.alpha.-D-glucopyranoside.脱苯甲酰化，然后在相同条件下与2，3，4，6-tetra-O-benzyl-1-O-(N-methylacetimidyl)-.beta.-D-galactopyranose缩合，得到四糖衍生物，该四糖衍生物被催化氢解成人B血型抗原决定簇O-.alpha.-L-fucopyranosyl-(1.fwdarw.2)-[O-.alpha.-D-galactopyranosyl-(1.fwdarw.3)]-O-.beta.-D-galactopyranosyl-(1.fwdarw.4)-2-acetamido-2-deoxy-D-glucopyranose，。
Treatment of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-.beta.-D-galactopyranosyl-.alpha.-D-glucopyranoside with benzaldehyde in the presence of Zncl, followed by regioselective benzoylation (N-benzoylimidazole in dichloromethane) provided crystalline benzyl 2-acetamindo-4-O-(3-O-benzoyl-4,6-O-benzylidene-.beta.-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-.alpha.-D-glucopyranoside. Condensation of this disaccharide with 2,3,4-tri-O-benzyl-1-O-(N-methylacetimidyl)-.beta.-L-fucopyranose in nitromethane in the presence of P-toluenesulfonic acid and molecular sieves 4 .ANG. gave benzyl O-(2,3,4-tri-O-benzyl-.alpha.-L-fucopyranosyl)-(1.fwdarw.2)-O-(3-O-benzyl-4,6-O-benzylidene-.beta.-D-galactopyranosyl)-(1.fwdarw.4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-.alpha.-D-glucopyranoside. Debenzoylation, followed by condensation with 2,3,4,6-tetra-O-benzyl-1-O-(N-methylacetimidyl)-.beta.-D-galactopyranose under the same conditions provided a tetrasaccharide derivative that was catalytically hydrogenolyzed into O-.alpha.-L-fucopyranosyl-(1.fwdarw.2)-[O-.alpha.-D-galactopyranosyl-(1.fwdarw.3)]-O-.beta.-D-galactopyranosyl-(1.fwdarw.4)-2-acetamido-2-deoxy-D-glucopyranose, the antigenic determinant of human blood group B.