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• W1556537897 abstract "Methyl-5-acetylamino-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosidonsäure-methylester (1) wurde über das 8,9-O-Isopropylidenderivat 2 mit Pyridiniumchlorochromat (PCC) oder Pyridiniumfluorochromat (PFC) in das 4-Ketoderivat 3 übergeführt (Schema 1). Mit Triphenyl-phosphan/Azodicarbonsäure-diethylester und Stickstoffwassersäure ergibt 2 das Oxazolinderivat 4, das mit Salzsäure in Methanol in den Methyl-4-O-acetyl-5-acetylamino-3,5-didesoxy-β-D-glycero-D-talo-2-nonulopyranosidonsäure-methylester (5a) und die Derivate 5b–d umgewandelt wird. Der Methyl-5-acetylamino-7,8-anhydro-4,9-bis-O-(tert-butyldimethylsilyl)-3,5-didesoxy-α-L-glycero-D-galacto-2-nonulopyranosidonsäure-methylester (6) und das analoge 7,8-Anhydro-β-D-glycero-L-altro-Derivat 8 wurden mit Chlortrimethylsilan und Natriumiodid zu den entsprechenden 8-Iod-8-desoxy-β-D-glycero-D-galacto- bzw. 8-Iod-8-desoxy-α-L-glycero-L-altro-2-nonulopyranosidonsäure-methylester-Derivaten 7b–d bzw. 9b geöffnet (Schema 2). 10 liefert mit N,N-Dimethylformamid-dimethylacetal über die Zwischenstufen 11 und 12 mit Acetanhydrid die Epoxide 6 und 8 oder mit Methyliodid den Methyl-5-acetylamino-4,9-bis-O-(tert-butyldimethylsilyl)-3,5,8-tridesoxy-7-O-form yl-8-iod-α-L-glycero-D-galacto-2-nonulopyranosidonsäure-methylester (13) und die 7-Desoxy-7-iod-β-D-glycero-L-altro-Derivate 14 und 14a. 13, 14 und 14a können mit Natriummethanolat in das 7,8-Anhydro-β-D-glycero-D-galacto-2-nonulopyranosidonsäure-methylester-Derivat 15 übergeführt werden, dessen 9-O-(tert-Butyldimethylsilyl)-Gruppe selektiv mit Tetrabutylammoniumfluorid unter Bildung von 15a entfernt werden kann (Schema 3). Transformations with N-Acetylneuraminic Acid, 2 From methyl 5-acetylamino-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester (1) the 8,9-O-isopropylidene derivative 2 was obtained, which was transformed with pyridinium chlorochromate (PCC) or pyridinium fluorochromate (PFC) into the 4-keto derivative 3 (Scheme 1). Treatment of 2 with triphenylphosphane/diethyl azodicarboxylate and hydrazoic acid yields the oxazoline derivative 4. Compound 4 can be converted with hydrochloric acid in methanol to give the methyl 4-O-acetyl-5-acetylamino-3,5-dideoxy-β-D-glycero-D-talo-2-nonulopyranosidonic acid methyl ester (5a) and the derivatives 5b - d. methyl 5-acetylamino-7,8-anhydro-4,9-bis–O-(tert-butyldimethylsilyl)-3,5-dideoxy-α-L-glycero-2-nonulopyranosidonic acid methyl ester (6) and the analogous 7,8-anhydro-β-D-glycero-L-altro derivative 8 were transformed with chlorotrimethylsilane and sodium iodide into the corresponding 8-iodo-8-deoxy-β-D-glycero-d-galacto- or the 8-iodo-8-deoxy-α-L-glycero-L-altro-2-nonulopyranosidonic acid methyl ester derivatives 7b-d or 9b, respectively (Scheme 2). Treatment of 10 with N,N-dimethylformamide dimethyl acetal yields - via the intermediates 11 and 12 - either with acetic anhydride the epoxides 6 and 8 or with methyl iodide the methyl 5-acetylamino-4,9-bis-O-(tert-butyldimethylsilyl)-3,5,8-trideoxy-7-O-formyl-8-iodo-α-L-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester (13) and the 7-deoxy-7-iodo-β-D-glycero-L-altro derivatives 14 and 14a. Reaction of 13, 14, or 14a with sodium methoxide yields the 7,8-anhydro-β-D_glycero-D-galacto-2-Nonulopyranosidonic acid methyl ester derivative 15, the 9-O_(tert-butyldimethylsilyl) group can be selectively removed with tetrabutylammonium fluoride to give 15a (Scheme 3). Structure elucidation was achieved by 1H NMR spectra of the corresponding acetates." @default.
• W1556537897 created "2016-06-24" @default.
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• W1556537897 date "1983-12-15" @default.
• W1556537897 modified "2023-10-09" @default.
• W1556537897 title "Strukturelle Abwandlungen anN-Acetylneuraminsäure, 2" @default.
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• W1556537897 doi "https://doi.org/10.1002/jlac.198319831202" @default.
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