WERNER RANK's research while affiliated with University of Ottawa and other places
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Publications (12)
N-Bromoacetamide, in the presence of a catalytic amount of sodium acetate, reacted smoothly with the nitroalkene moiety of 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-enofuranose (1) by addition of bromine and an acetamido group across the olefinic double bond, with concomitant introduction of a second bromine atom at C-6. Th...
Die Halogenierung von Methyl-4,6-O-benzyliden-3-desoxy-3-nitro-hexopyran siden mit α-D-talo-, β-D-galacto- und α-D-galacto-Konfiguration und von 2, Didesoxy-3-nitro-β-D-lyxo- und α-D-lyxo-Analogen führt zu 3-Halogen-3-des 3-nitro-Derivaten.
Die Reduktion der isomeren Nitrohexenopyranoside (II) mit Na-boranat gibt die gesättigten Nitroverbindungen (I) (87 bzw. 91% Ausbeute); mit Zn-Essigsäure werden aus (I) die Oxime (III) erhalten (87 bzw. 88%), die mit Lävulinsäure/HCI die Oxozucker (IV) liefern.
In einer Neuuntersuchung wird durch eingehende NMR-Analyse die quantitative Epimeren-Verteilung der aus dem Dialdehyd (I) [durch Nitromethan-Cyclisierung, Deionisierung und Umsetzung mit Benzaldehyd/Zn-chlorid (bekannte Methode)] gebildeten isomeren Acetale (IIa), (IIb), (IIIa) und (IIIb) ermittelt.
Durch Reaktion mit wäßrigem 30%ige-r-n- Wasserstoffperoxid bei pH 8-9 in äthanolischer Lösung entstehen in hoher Stereoselektivität aus dem erythro- Hexenopyranosid (I) das Mannopyranosid (II), aus dem (I)-Anomeren (IV) das Allopyranosid (V) und aus dem threo-Hexenopyranosid (VI) das Talopyranosid (VII).
Bei Acetylierung des Mannosids (Ia) und des Galaktosids (IIa) mit Acetylchlorid und Triäthylamin in Äther entstehen die erwarteten 2-O-Acetylderivate(Ib) bzw. (IIb).
Der Umfang der Nitronat-Bildung in sieben Methyl-4,6-O-benzyliden-3-desoxy- 3-nitro-hexopyranosiden und vier Methyl-4,6-O-benzyliden-2,3-didesoxy-3-nitro-hexopyranosiden in verdünnter KOH-Lösung wird" UV-spektroskopisch untersucht.
Action of hydrogen peroxide in a weakly alkaline medium upon nitroolefinic sugar derivatives led to α-nitroepoxides in excellent yields. Thus, methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-α-D-erythro-hex-2-enopyranoside (1), its β-anomer 2, and its α-D-threo epimer 3 stereospecifically gave methyl 2,3-anhydro-4,6-O-benzylidene-3-C-nitro-α-D-mannopy...
Whereas acetylation of methyl 4,6-O-benzylidene-3-deoxy-3-nitro-β-D-mannopyranoside (1) and its β-D-galacto isomer 2 with acetyl chloride and triethylamine in ether furnished the expected 2-O-acetylated nitro glycosides, 1a and 2a, the same method applied to the α-D-talo isomer 3 gave the 2-O-acetyl derivative of the corresponding nitronic acid – a...
The extent of nitronate formation in seven methyl 4,6-O-benzylidene-3-deoxy-3-nitrohexopyranosides and four methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitrohexopyranosides in dilute potassium hydroxide solution was compared by means of u.v. spectroscopy. Considerable differences were found to exist in the nitromethylene acidities, and these were correl...
Die selektive Tritylierung des Glucopyranosids (Ia) liefert das 6-Tritylderivat (Ib) (65% Ausbeute), das durch Behandlung mit Acetylchlorid in Gegenwart von Triäthylamin in das Derivat (Ic) (67%) und durch Behandlung mit Acetanhydrid in Gegenwart von B-trifluorid in das Derivat (Id) (78%) übergeführt wird.
