Synthesis of glycosyl phosphonates and related compounds

✍ Scribed by Andrea Vasella; Gisèle Baudin; Luigi Panza

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 810 KB
• Volume: 2
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520020117

✦ Synopsis

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, a n advanced intermediate 59 for the synthesis of diphosphonate-phosphate analogues of 50 is obtained by a n addition-eliminationaddition 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-0benzylglucopyranosylidene carbene. The phosphine oxides 61 and 62 were also obtained by reaction of the glycosyl acetate 18 with methyl diphenylphosphinite.