Ethyl 2-acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-d-glycopyranoside as a versatile GlcNAc donor

Boysen, Mike M. K.; Gemma, Emiliano; Lahmann, Martina; Oscarson, Stefan

doi:10.1039/b503651h

Cited by 85 publications

(53 citation statements)

References 11 publications

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“…16,17 We anticipated that oxazolidinone protected thioglycosyl acceptor 2 may lead to higher glycosylation yield and the resulting disaccharide can function as a glycosyl donor. 18 To investigate the influence of N-protecting groups on our glycosylation methodology, glycosyl acceptors 2, 3, and 4 were prepared. The azido moiety is unsuitable as an N-protecting group for one-pot synthesis of β-linked oligoglucosamines because it is a well known non-participatory group favoring the formation of α-anomer when used in a donor.…”

Section: Resultsmentioning

confidence: 99%

Iterative one-pot syntheses of chitotetroses

Huang

Wang

et al. 2006

Carbohydrate Research

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Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis.

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Section: Resultsmentioning

confidence: 99%

Iterative one-pot syntheses of chitotetroses

Huang

Wang

et al. 2006

Carbohydrate Research

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“…Only recently, the first case of endocyclic cleavage of pyranosides under weak acidic conditions was proposed, as a reaction mechanism for anomerization reactions from the β to the α anomer, observed in pyranosides carrying 2N, 3O-trans-oxazolidinone groups in the presence of BF 3 -OEt 2 (116)(117)(118)(119)(120)(121)(122)(123)(124)(125). The general hypothesis of the anomerization starts with the endocyclic cleavage followed by bond rotation and final cyclization (Fig.…”

Section: H Chemistry Of Endocyclic Cleavage Reactionsmentioning

confidence: 99%

Computational Chemistry on Chemical Glycosylations

Satoh

Nukada

2014

TIGG

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The glycosylation reaction, which makes glycosidic linkages to develop a sugar chain, is one of the essential reactions in the realms of glycoscience. An understanding of mechanistic details of this key reaction will not only give researchers deeper insights on the nature of biochemical glycosylation reactions but will further the development of synthetic strategies in a rational way. In the present article we will overview the studies on mechanisms of glycosylation reactions, focusing on those using computational approaches. We review theoretical studies on general mechanistic issues, extensively discussing them in conjunction with the influence of neighboring groups and solvents, as well as stereoelectronic effect. The influence of a glycosyl donor's conformational flexibility on its reactivity/stereoselectivity and the debate about exocyclic or endocyclic cleavage of pyranoside rings are also described.

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“…317 In contrast, glycosidation of similar ethylthio glycoside in the presence of NIS/AgOTf provided complete 1,2-trans selectivity. 349 Analogous N-acetylated derivatives and their application will be discussed below in Section 4.2.3.…”

Section: Miscellaneous Monosubstituted Derivativesmentioning

confidence: 99%