Synthesis of glycosyl phosphonates and related compounds

Andrea Vasella, Gisèle Baudin, Luigi Panza

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

The synthesis of glycosylphosphonates, isopolar, nonisosteric analogues of glycosylphosphates, from halonitro ethers, glycosyl acetates, or glycosyl trichloroacetimidates is reviewed. A new approach to phosphonate analogues of myo‐inositol trisphosphate (50) is described. Based on a hypothetical reaction mechanism for the formation of thioethers from a glyoxalase I inhibitor, an advanced intermediate 59 for the synthesis of diphosphonate–phosphate analogues of 50 is obtained by an addition–elimination–addition sequence from 54. Finally, glucosylphosphines, characterized as the corresponding phosphine oxides 61 and 62 have been prepared from the glycosylidene diazirine 60, a precursor of the tetra‐O‐benzylglucopyranosylidene carbene. The phosphine oxides 61 and 62 were also obtained by reaction of the glycosyl acetate 18 with methyl diphenylphosphinite.

Lingua originaleInglese
pagine (da-a)151-161
Numero di pagine11
RivistaHeteroatom Chemistry
Volume2
Numero di pubblicazione1
DOI
Stato di pubblicazionePubblicato - feb 1991

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