TY - JOUR
T1 - Synthesis of glycosyl phosphonates and related compounds
AU - Vasella, Andrea
AU - Baudin, Gisèle
AU - Panza, Luigi
PY - 1991/2
Y1 - 1991/2
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84986384822&partnerID=8YFLogxK
U2 - 10.1002/hc.520020117
DO - 10.1002/hc.520020117
M3 - Article
SN - 1042-7163
VL - 2
SP - 151
EP - 161
JO - Heteroatom Chemistry
JF - Heteroatom Chemistry
IS - 1
ER -