Synthesis of 3-substituted (azido, acylthio, chloro or fluoro)-2,3-dideoxy-D-erythro-pentoses and 3-methyl-3-substituted-2,3-dideoxy-D-erythro-pentoses

Autor:	Ving J. Lee, Yuri E. Raifeld, Igor E. Mikerin, Lubov L. Zilberg, Galina Ya. Vid, Stanley A. Lang, Antonia A. Nikitenko, B. M. Arshava
Rok vydání:	1994
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Acetal Diastereomer Enantioselective synthesis Epoxide Glycoside Pentose Biochemistry chemistry.chemical_compound chemistry Aldose Reagent Drug Discovery
Zdroj:	Tetrahedron. 50:8603-8616
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)85335-7
Popis:	The enantioselective synthesis of 3-substituted and 3-methyl-3-substituted 2,3-dideoxy-D- erythro -pentoses from (3 R ,4 R )-1,1-diethoxy-3,4-epoxypentane-5-ol, (3 R ,4 R) -1,1-diethoxy-3,4-epoxy-3-methylpentane-5-ol and (2 R ,3 R )-2,3-epoxy-5-hexen-1-ol is reported. The key step is cleavage of the oxirane ring by Ti(O- i -Pr) 3 X class reagents followed by selective cyclization of the acyclic acetals to the furanosides. Fluorination with the complex of titanium (IV) iso -propoxide - titanium (IV) fluoride provides an enantioselective synthesis of 3-fluoro-2,3-dideoxy-D- erythro -pentose and 3-fluoro-3-methyl-2,3-dideoxy-D- erythro -pentose.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::afd61b5a3188ed5bb6890bbeb2ef184b https://doi.org/10.1016/s0040-4020(01)85335-7 Zobrazit plný text záznamu