Influence of substitution at the 5α-Position on the side chain conformation of glucopyranosides

Autor:	David Crich, Michael G. Pirrone, Parasuraman Rajasekaran
Rok vydání:	2021
Předmět:	Steric effects education.field_of_study Gauche effect Chemistry Organic Chemistry Population Substitution (logic) General Medicine Biochemistry Article Analytical Chemistry Crystallography Glucosides Pyrones Position (vector) Carbohydrate Conformation Side chain education Conformational isomerism
Zdroj:	Carbohydr Res
ISSN:	0008-6215
Popis:	We describe the preparation of methyl 5α-methyl-α- d -glucopyranoside and of 5α-fluoro-β- d -glucopyranose per acetate and the NMR-based conformational analysis of their side chains. Both the 5α-methyl and 5α-fluoro substituents increase the population of the gauche,gauche side chain conformer to the extent that it becomes the predominant conformation. In the 5α-methyl series this is attributed to steric effects, whereas in the 5α-fluoro series the optimization of attractive gauche effects is the more likely reason.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d278f28c999be2d1f0945e261987c1c2 https://doi.org/10.1016/j.carres.2021.108254 Zobrazit plný text záznamu Full Text from ScienceDirect