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- Title
Practical And Economic Synthesis Of 2,3-O-Isopropylidene-DErythrose.
- Authors
Zheng Yang Lee; Jhi Biau Foo; Wibowo, Agustono; Mohammat, Mohd Fazli
- Abstract
Introduction: 2,3-O-isopropylidene-D-erythrose has been a useful chiral precursor involved in the total synthesis of several natural products such as the leukotrienes, pyrrolizidine and indolizidine alkaloids. However, previous published protocols used expensive chemicals/reagents in the synthesis scheme. In this study, we synthesised D-erythrose from erythorbic acid with inexpensive and commercially available chemicals/reagents. Methods: D-erythrose was synthesised from published protocol with modification. Briefly, sodium erythorbate was treated with hydrogen peroxide to yield a mixture of D-erythronolactone, oxalic acid and sodium chloride. Further exposure to anhydrous acetone and p-toluenesulfonic acid monohydrate gave the acetonide form of D-erythronolactone. The corresponding acetonide was then partially reduced into the lactol in excellent yield by using sodium bis(2-methoxyethoxy-aluminium hydride. Purification of the products was carried out using the classical column chromatography Si-gel G60 (230-400 mesh, Merck). The 1H and 13C NMR spectra was registered in CDCl3 with Joel Resonance ECZ400S 400 MHz (1H) and 100 MHz (13C) using TMS as the internal standard. The specific optical rotation was determined using Anton Paar MCP 500 polarimeter. Results: 2,3-O-Isopropylidene-D-erythrose was obtained as colourless oil in the overall yield of 82% from the corresponding protected lactone. Conclusion: Selectively protected D-erythrose was easily prepared in substantial quantity as a mixture of enantiomers from the inexpensive chiral starting material. This may give a cheaper cost of production for clinically used drugs.
- Subjects
MERCK KGaA; PYRROLIZIDINES; OPTICAL rotation; COLUMN chromatography; ACYL chlorides; HYDROGEN peroxide; OXALIC acid
- Publication
Malaysian Journal of Medicine & Health Sciences, 2022, Vol 18, p34
- ISSN
1675-8544
- Publication type
Abstract