Synthesis of the salmonella type E1 core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides
Synthesis of the salmonella type E1 core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides
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DOI：
10.1021/jo0108818
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发表时间：
2002-07-12
影响因子：
3.6
通讯作者：
Li, HM
中科院分区：
文献类型：
--
作者：
Crich, D;Li, HM
提出了沙门氏菌 E-1 类核心三糖显色糖苷的合成，其中代表四种主要糖苷键中的三种的所有三个糖苷键，即 1,2-顺式赤道键、1,2-反轴键和 1,2-反赤道键，均由硫代糖苷供体在一组条件下通过以下组合激活而形成： 1-(苯亚磺酰基)哌啶和三氟甲磺酸酐。发现2,3-O-羰基-和2,3-O-异亚丙基-α-L-吡喃鼠李糖苷在这些条件下是高度α-选择性的鼠李糖基供体。
A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.