Syntheses of alpha- and beta-C-glucopyranosyl serines from a common intermediate

Autor:	Trevor A Daly, David R. Calabrese, Rebecca Greaves, Ernest G. Nolen, Laurence A Donahue
Rok vydání:	2008
Předmět:	chemistry.chemical_classification Esterification Molecular Structure Stereochemistry Alkene Organic Chemistry Alpha (ethology) Stereoisomerism Biochemistry Transposition (music) Glucose chemistry Cyclization Serine Molecule Physical and Theoretical Chemistry Beta (finance) Lactone
Zdroj:	Organic letters. 10(21)
ISSN:	1523-7052
Popis:	A versatile synthesis leading to either C-linked alpha- or beta-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the alpha-linkage. A transposition of these last steps leads to the beta-linked isomer selectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::223cee7643d9759c29199c4f0fb49d1b https://pubmed.ncbi.nlm.nih.gov/18821764 Zobrazit plný text záznamu