Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 221-227 |
| Journal | Carbohydrate research |
| Volume | 299 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 30 Apr 1997 |
Keywords
- catalyst immobilization
- d-glucuronic acid
- naocl-tmepo oxidation
- α-d-glucopyranuronate 1-fluoride
- α-d-glucopyranuronate 1-phosphate
- β-d-glucopyranuronate 1-phosphate
Cite this
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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. / Heeres, André; Van Doren, Henk A.; Gotlieb, Kees F.; Bleeker, Ido Pieter.
In: Carbohydrate research, Vol. 299, No. 4, 30.04.1997, p. 221-227.Research output: Contribution to journal › Article › Academic › peer-review
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 - 1997/4/30
Y1 - 1997/4/30
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
VL - 299
SP - 221
EP - 227
JO - Carbohydrate research
JF - Carbohydrate research
SN - 0008-6215
IS - 4
ER -