Cardiac glycosides: 3. synthesis of β-D-digitoxose analogues

Autor:	Dwight S. Fullerton, Douglas C. Rohrer, Tamboue Deffo, Kouichi Yoshioka, Masaru Kihara
Rok vydání:	1984
Předmět:	chemistry.chemical_classification Strain (chemistry) Chemistry Stereochemistry medicine.medical_treatment Organic Chemistry Glycoside Biological activity Nuclear magnetic resonance spectroscopy Biochemistry Acetonide Steroid Drug Discovery medicine Lactone Cardiac glycoside medicine.drug
Zdroj:	Tetrahedron. 40:1121-1133
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)99316-0
Popis:	Earlier studies have shown that the β-D-digitoxose (2,6-dideoxy-β-D-mannopyranose) directly attached to the cardiac glycoside steroid C3 has the greatest effect on biological activity. This report describes the synthesis of eight digitoxosides (2a-9a), with widely varying cyclic and acyclic C17β-side groups, and the corresponding C3',C4'-acetonides (2b-9b). NMR analysis of conformational strain introduced by the acetonide groups is supported by crystallographic analysis of the sugars' torsion angles.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::618ea5089ba45e8a4469e565b0e0db32 https://doi.org/10.1016/s0040-4020(01)99316-0 Zobrazit plný text záznamu