Stereospecific synthesis of methyl D,L-hex-2-ulopyranosides from furan compounds

Autor:	Maria H. Burzyńska, Osman Achmatowicz
Rok vydání:	1982
Předmět:	Steric effects Hydroxylation chemistry.chemical_compound Stereospecificity chemistry Stereochemistry Furan Organic Chemistry Drug Discovery Ring (chemistry) Biochemistry
Zdroj:	Tetrahedron. 38:3507-3513
ISSN:	0040-4020
DOI:	10.1016/0040-4020(82)85036-9
Popis:	2-Benzyloxymethyl-5-hydroxymethylfuran was converted, according to the known method, into methyl 1-O-benzyl-3,4-dideoxy- d,l -hex-3-en-2-ulopyranos-5-ulose. Reduction of the latter and hydroxylation or epoxidation, followed by the oxirane ring opening, afforded the title compounds with α-sorbo-, β-fructo-, α-tagato- and α-pisco- configuration. The steric course of reduction, hydroxylation and epoxidation reactions were examined.
Databáze:	OpenAIRE
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