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- W2949259712 abstract "Starting from the dianhydro-epi-inositol 10 (available ultimately from benzene) an expedient total synthesis of enantiomerically pure (+)/(−)-de-O-methylfortamines (derivatives) has been developed. Key steps are the regiospecific epoxide openings which occur intramolecularly in the diepoxybis(urethane) 11 and intermolecularly by (+)-1-phenylthylamine in the epoxyurethanes rac-13. The diastereomeric adducts (30, 32) are quantitatively separated by crystallization/chromatogrphy. Following hydrogenation, natural and nonnatural cis-1,4-inosadiamines are obtained optically pure [e.g. fortamine (−)-1, ent-fortamine (+)-1, 3-O-demethylfortamine (−)-38, ent-3-O-demethylfortamine (+)-38]. This approach, which was optimized by numerous model reactions, allows wide chemical modifications and leads among others to 3-O-demethylfortamine and ent-fortamine derivatives in which only the (6)4-OH-group, the one to be glycosidated, remains unprotected.Aminoglycosid-Antibiotika – Fortamin-Aglyca Totalsynthese, Racemattrennung, chemischen ModifizierungenAusgehend von Dianhydro-epi-inosit 10 (letztlich erhaltlich aus Benzol) wurde eine leistungsfahige Synthese fur enantiomerenreine (+)/(−)-Des-O-methylfortamine (Derivate) entwickelt. Zentrale Schritte sind die regiospezifischen Epoxidoffnungen, intramolekular beim Diepoxybis(urethan) 11 und intermolekular mit (+)-1-Phenylethylamin bei den Epoxyurethanen rac-13. Die diastereomeren Addukte (30, 32) konnen verlustfrei durch Kristallisation/Chromatographie getrennt werden. Nach hydrierender Spaltung werden naturliche und nicht naturliche cis-1,4-Inosadiamine enantiomerenrein erhalten [z. B. Fortamin (−)-1, ent-Fortamin (+)-1, 3-O-Desmethylfortamin (−)-38, ent-3-O-Desmethylfortamin (+)-380]. Der in zahlreichen Modellreaktionen optimierte Syntheseweg erlaubt breite chemische Modifizerungen und fuhrt u.a.zu 3-O-Desmethylfortamin- und ent-Fortamin-Derivaten, in denen nur die zur Glycosidierung gebrauchte (6)4-OH-Gruppe ungeschutzt bleibt." @default.
- W2949259712 created "2019-06-27" @default.
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- W2949259712 date "1987-05-05" @default.
- W2949259712 modified "2023-09-27" @default.
- W2949259712 title "ChemInform Abstract: Aminoglycoside Antibiotics - Fortamine Aglyca. Total Synthesis, Optical Resolution, Chemical Modifications." @default.
- W2949259712 cites W2078359768 @default.
- W2949259712 doi "https://doi.org/10.1002/chin.198718361" @default.
- W2949259712 hasPublicationYear "1987" @default.
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