水杨基硫代糖苷类化合物作为寡糖合成的无臭硫代糖苷替代品的反应性和立体选择性评价

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Journal of Carbohydrate Chemistry Pub Date : 2021-01-01 DOI:10.1080/07328303.2021.1921787

Hirofumi Dohi , Risa Sakurai , Manami Tamura , Ryota Komai , Yoshihiro Nishida

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引用次数: 1

摘要

摘要本文中，o-（甲氧羰基）苯基硫糖苷[或（甲基）水杨酸基1-硫糖苷]被评估为无恶臭的硫糖苷替代品。邻甲氧羰基有望协助离去基团的离去。当N-碘代琥珀酰亚胺和三氟甲磺酸用作促进剂时，水杨酸基硫代糖苷表现出高的反应性和糖基化产率。这些硫代糖苷在二氯甲烷中的糖基化反应显示出与苯基硫代糖苷类似的反应性和立体选择性。在二氯甲烷中用全-O-苄基水杨酸基硫代糖苷进行的糖基化反应显示出1，2-顺式选择性，而在腈中进行的相同反应主要提供1，2-反式糖苷。相反，用全-O-苯甲酰基硫代糖苷进行糖基化仅提供1，2-反式糖苷。这些结果有力地表明，水杨酸基硫代糖苷可以作为苯基硫代糖苷的无恶臭替代品。图形摘要

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Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis

Herein, o-(methoxycarbonyl)phenyl thioglycosides [or (methyl)salicyl 1-thioglycosides] were evaluated as non-malodorous thioglycoside alternatives. The o-methoxycarbonyl group was expected to assist in the departure of leaving group. Salicyl-type thioglycosides exhibited high reactivity and glycosylation yields when N-iodosuccinimide and trifluoromethanesulfonic acid were used as promoters. Glycosylation with these thioglycosides in dichloromethane showed similar reactivity and stereoselectivity as those of phenyl thioglycosides. Glycosylation with per-O-benzyl salicyl-type thioglycosides in dichloromethane showed 1,2-cis-selectivity, while the same reaction in nitriles afforded predominantly 1,2-trans glycosides. In contrast, glycosylation with per-O-benzoyl thioglycosides afforded exclusively 1,2-trans glycosides. These results strongly suggest that salicyl-type thioglycosides can serve as non-malodorous alternatives for phenyl thioglycosides.

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来源期刊

Journal of Carbohydrate Chemistry 化学-生化与分子生物学

CiteScore

2.10

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Carbohydrate Chemistry serves as an international forum for research advances involving the chemistry and biology of carbohydrates. The following aspects are considered to fall within the scope of this journal: -novel synthetic methods involving carbohydrates, oligosaccharides, and glycoconjugates- the use of chemical methods to address aspects of glycobiology- spectroscopic and crystallographic structure studies of carbohydrates- computational and molecular modeling studies- physicochemical studies involving carbohydrates and the chemistry and biochemistry of carbohydrate polymers.