Trifluoromethanesulfonic Acid Efficiently Catalyzed the Intramolecular Glycosidation of 1-C-Alkyl-d-hexopyranoses to Form the Anhydroketopyranoses Having 6,8-Dioxabicyclo[3.2.1]octane Structures

Autor:	Kazuhide Matsumura, Yoshiki Oda, Takashi Yamanoi, Sho Matsuda
Rok vydání:	2005
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Chemistry Intramolecular force Organic Chemistry Medicinal chemistry Alkyl Catalysis Octane
Zdroj:	Synlett. 2005:2973-2977
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-2005-921912
Popis:	The intramolecular glycosidation of the 1-C-alkyl-D-hexopyranose derivatives to form the anhydroketopyranoses having 6,8-dioxabicyclo[3.2.1]octane structures was investigated. We synthesized several l-C-alkyl-2,3,4-tri-O-benzyl-D-hexopyranoses and found that only 5 mol% trifluoromethanesulfonic acid efficiently promoted the intramolecular glycosidation to afford the desired anhydroketopyranoses in good yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c5a2fbb232d015c751148b90960bcafc https://doi.org/10.1055/s-2005-921912 Zobrazit plný text záznamu