TY - JOUR
T1 - Synthesis of α- and β-D-glucopyranuronate 1-phosphate and α-D-glucopyranuronate 1-fluoride: intermediates in the synthesis of D-glucuronic acid from starch
AU - Heeres, André
AU - Van Doren, Henk A.
AU - Gotlieb, Kees F.
AU - Bleeker, Ido Pieter
PY - 1997/4/1
Y1 - 1997/4/1
N2 - The title uronates were prepared by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) catalysed sodium hypochlorite oxidation of α- and β-D-glucopyranosylphosphate (α-/β-Glc-1-P) and α-D-glucopyranosyl fluoride (α-Glc-1-F). Quantitative recovery of the TEMPO catalyst was achieved by azeotropic distillation of a small part of the reaction mixture. Also, a heterogeneous catalyst system was prepared by immobilisation of 4-oxo-tetramethyl-1-piperidinyloxy (OTEMPO) on amino-functionalized silica. The protected uronates were hydrolysed to yield D-glucuronate. Since α- and β-Glc-1-P and α-Glc-1-F can be obtained from starch in one step, D-glucuronic acid is now available from starch in a convenient three-step sequence.
AB - The title uronates were prepared by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) catalysed sodium hypochlorite oxidation of α- and β-D-glucopyranosylphosphate (α-/β-Glc-1-P) and α-D-glucopyranosyl fluoride (α-Glc-1-F). Quantitative recovery of the TEMPO catalyst was achieved by azeotropic distillation of a small part of the reaction mixture. Also, a heterogeneous catalyst system was prepared by immobilisation of 4-oxo-tetramethyl-1-piperidinyloxy (OTEMPO) on amino-functionalized silica. The protected uronates were hydrolysed to yield D-glucuronate. Since α- and β-Glc-1-P and α-Glc-1-F can be obtained from starch in one step, D-glucuronic acid is now available from starch in a convenient three-step sequence.
KW - catalyst immobilization
KW - d-glucuronic acid
KW - naocl-tmepo oxidation
KW - α-d-glucopyranuronate 1-fluoride
KW - α-d-glucopyranuronate 1-phosphate
KW - β-d-glucopyranuronate 1-phosphate
U2 - 10.1016/s0008-6215(97)00030-x
DO - 10.1016/s0008-6215(97)00030-x
M3 - Article
SN - 0008-6215
VL - 299
SP - 221
EP - 227
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 4
ER -