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Préparation de phosphonates de sucres ramifiés par addition nucléophile conjuguée. Communication préliminaire

✍ Scribed by Jean M. J. Tronchet; Jean-Richard Neeser; Luis Gonzalez; Etienne J. Charollais


Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
173 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis


Preparation of unsaturated sugars phosphonates using nucleophilic conjugate addition

Different types of phosphorus nucleophiles underwent conjugate addition reaction with one of the branched‐chain sugars 4, 5 or 11 the addition taking place either on the endo or the exo face of the furanose ring (or on both faces in the case of 11). The configuration at C(3) of these new phosphorus‐bearing types of sugars as well as the configuration at the phosphorus atom of the cyclic phosphinates 9 and 10 was established by NMR. (^3^J~P,H–C(2)~, ^3^J~P,C(1)~). Small amounts (7%) of the spiro enol phosphonate 16 were formed when 11 reacted with trimethyl phosphite.


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