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• W2022122022 abstract "The vicinal cis-oxyamination of ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (1) and of methyl 4-O-acetyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranoside (11) as well as of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-(17) and -D-lyxo-hex-1-enitol (23) with Chloramine T-osmium tetraoxide was investigated (Sharpless reaction). The hex-2-enopyranosides 1 and 11 yielded the corresponding 3-deoxy-3-p-toluenesulfonamido-and 2-deoxy-2-p-toluenesulfonamido-hexopyranosides with the manno configuration in the ratio 2:1. The glycals 17 and 23 reacted with formation of the corresponding α-D-gluco and α-D-galactoN-tosyl-glycosylamines and of the 2-deoxy-2-p-toluenesulfonamidoglycoses in the ratio 3:1. The stereospecifity and the regioselectivity of the reactions are discussed. Quantum chemical calculations on models for the hex-2-enopyranosides 1 and 11 suggest a [3+2] cycloaddition of the N-tosylimido osmium(VIII) oxide in preference to a [2+2] mechanism with participation of the metal species. The preparative importance of the oxyamination reaction is demonstrated by a simple synthesis of N-acetyl-mycosamine. Die vicinale cis-Oxyaminierung von Ethyl-4,6-di-O-acetyl-2,3-didesoxy-α-D-erythro-hex-2-enopyranosid (1) und Methyl-4-O-acetyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranosid (11) sowie von 3,4,6-Tri-O-acetyl-1,5-anhydro-2-desoxy-D-arabino- (17) und D-lyxo-hex-1-enitol (23) mit Chloramin-T-Osmiumtetraoxid wird untersucht (Sharpless Reaktion). Die Hex-2-enopyranoside 1 und 11 liefern im Verhältnis 2:1 die entsprechenden manno-konfigurierten 3-Desoxy-3-p-toluolsulfonamido-und 2-Desoxy-2-p-toluolsulfonamido-hexopyranoside, während die Glykale 17 und 23 im Verhältnis 3:1 zu den gluco- bzw. galacto-konfigurierten N-Tosylglycosylaminen und 2-Desoxy-2-p-toluolsulfonamido-glycosen reagieren. Die Ursachen für die Stereospezifität und Regioselektivität werden diskutiert. Quantenchemische Rechnungen an Modellen für die Hex-2-enopyranoside 1 und 11 legen eine [3+2] Cycloaddition des N-Tosylimido-osmium(VIII) oxids und nicht eine [2+2] Addition unter Beteiligung des Metalls nahe. Die präparative Bedeutung der Oxyaminierungsreaktion wird durch eine einfache Synthese des N-acetylmycosamins demonstriert." @default.
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• W2022122022 title "Aminodesoxyzucker und glycosylamin-synthesen durch oxyaminierung von hex-2-enopyranosiden und hex-1-enitolen. Synthese des N-acetylmycosamins" @default.
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