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Préparation de phosphonates de sucres ramifiés par addition nucléophile conjuguée . Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Neeser JeanRichard,
Gonzalez Luis,
Charollais Etienne J.
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620631
Subject(s) - chemistry , conjugate , phosphonate , nucleophile , phosphorus , furanose , ring (chemistry) , medicinal chemistry , stereochemistry , nucleophilic addition , organic chemistry , catalysis , mathematical analysis , mathematics
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.