Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile

Amarasekara Harsha; Crich David

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Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile

机译：邻二甲苯二醇的唾液酸单酯的合成和分子内糖基化。供体构型和氮保护基对环化产率和选择性的重要性; N-唾液酸乙酰胺的分离和表征，表明乙腈参与

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The synthesis and cyclization reactions, leading to spirocyclic medium ring-sized diolides, of o-(hydroxymethyl)xylylene monoesters of sialyl thioglycosides is described. Cyclization yields and stereoselectivities are found to vary as a function of the anomeric stereochemistry of the thioglycoside and of the N5 protecting group, and these effects are discussed in terms of the reaction mechanism. Cyclization in the presence of acetonitrile results in the isolation and characterization of a Ritter-type N-sialyl acetamide, which affords strong evidence for the participation of acetonitrile in the form of sialyl nitrilium ions. (C) 2016 Elsevier Ltd. All rights reserved.

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《Carbohydrate research》 |2016年第null期|共8页
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Amarasekara Harsha; Crich David;
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正文语种 eng
中图分类有机化学;
关键词
N-Glycosyl amide; Lactonization; Sialic acid; Spirodiolide; Thioglycoside; Ritter reaction;

机译：N-糖基酰胺内酯化唾液酸螺二糖硫糖苷里特反应;

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1. Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile [J] . Amarasekara Harsha, Crich David Carbohydrate research . 2016,第Null期

机译：邻二甲苯二醇的唾液酸单酯的合成和分子内糖基化。供体构型和氮保护基对环化产率和选择性的重要性; N-唾液酸乙酰胺的分离和表征，表明乙腈参与
2. Synthesis and Intramolecular Glycosylation of Sialyl Mono-esters of o-Xylylene Glycol. The Importance of Donor Configuration and Nitrogen Protecting Groups on Cyclization Yield and Selectivity; Isolation and Characterization of a N-Sialyl Acetamide Indicative of Participation by Acetonitrile [O] . Harsha Amarasekara, David Crich -1

机译：邻二甲苯基乙二醇的唾液酸单酯的合成和分子内糖基化。供体构型和氮保护基对环化产率和选择性的重要性；指示乙腈参与的N-唾液酸乙酰胺的分离和表征
3. Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile [O] . Harsha Amarasekara, David Crich 2016

机译：邻二甲基二醇的SiaLyl单酯的合成与分子内糖基化。供体构型和氮保护组对环化产量和选择性的重要性;乙腈参与的N-SiAlyl乙酰胺的分离与表征

Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile

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