Benzyliden-verbindungen der pentonsäuren und pentonsäure-lactone

Add time:07/21/2019    Source:sciencedirect.com

Di-O-benzylidene derivatives of pentonic acids may be readily prepared by oxidation of the di-O-benzylidene-aldehydo-pentoses with chromium trioxide in N,N-dimethylformamide or by saponification of the corresponding methyl esters. Treatment of ammonium D-xylonate with benzaldehyde and hydrochloric acid gives the di-O-benzylidene-D-xylonic acid, whereas the D-ribonate and D-lyxonate salts give the 3,5-O-benzylidene-pentono-1,4-lactones. With benzaldehyde and zinc chloride, the methyl pentonates variously give the di- and mono-O-benzylidene derivatives and the mono-O-benzylidenepentonolactones. The structures of the di-O-benzylidene derivatives obey the rules of Hann and Hudson. The O-benzylidene-pentonolactones give the corresponding amides and hydrazides on treatment with ammonia and hydrazine hydrate, respectively; reduction with lithium aluminium hydride gives the O-benzylidenepentitols.

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