CHEMICAL SYNTHESIS OF 2-O-(ALPHA-L-FUCOPYRANOSYL)-3-O-(ALPHA-D-GALACTOPYRANOSYL)-D-GALACTOSE- TERMINAL STRUCTURE OF BLOOD-GROUP-B ANTIGENIC DETERMINANT
CHEMICAL SYNTHESIS OF 2-O-(ALPHA-L-FUCOPYRANOSYL)-3-O-(ALPHA-D-GALACTOPYRANOSYL)-D-GALACTOSE- TERMINAL STRUCTURE OF BLOOD-GROUP-B ANTIGENIC DETERMINANT
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DOI：
10.1021/ja00847a034
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发表时间：
1975-01-01
影响因子：
15
通讯作者：
DRIGUEZ, H
中科院分区：
文献类型：
--
作者：
LEMIEUX, RU;DRIGUEZ, H
描述了包括3，4-O-（乙基原乙酰基）中间体的封闭程序，以制备2，2，2-三氯乙基4，6-二-O-乙酰基-2-O-（三-O-苄基-α L-吡喃岩藻糖基）-β-D-吡喃半乳糖苷，其继而在溴离子催化条件下使用分子筛以吸收释放的溴化氢与四-O-苄基-D-吡喃半乳糖基溴进行缩合。将主要产物去封闭，得到与标题化合物的真实样品相同的三糖。由模型实验产生的方法提供了2-0-（aL-吡喃岩藻糖基）-D-半乳糖和3-0-（aD-吡喃半乳糖基）-D-半乳糖的新合成。记录并归属C13 NMR谱。
Blocking procedures are described, including a 3, 4-0-(ethyl orthoacetyl) intermediate, to prepare 2, 2, 2-trichloroethyl 4, 6-di-0-acetyl-2-0-(tri-0-benzyl-aL-fucopyranosyl)-/3-D-galactopyranoside which, in turn, was condensed under bromide ion catalyzed conditions using molecular sieve to absorbthe liberated hydrogen bromide with tetra-O-benzyl-D-galactopyranosyl bromide. Deblocking of the main product provided a trisaccharide which was identical with an authentic sample of the title compound. Procedures arising from model experiments provided new syntheses of 2-0-(aL-fucopyrano-syl)-D-galactose and 3-0-(aD-galactopyranosyl)-D-galactose. C13 NMR spectra are recorded and assigned.