PMID: 11674212Oct 25, 2001Paper

Synthesis of 1-Deoxy-D-xylulose and 1-Deoxy-D-xylulose-5-phosphate

The Journal of Organic Chemistry
Brian S J Blagg, C D Poulter

Abstract

1-Deoxy-D-xylulose (4) and the corresponding 5-phosphate (5) are substrates for the first pathway-specific enzymes in the biosynthesis of thiamine diphosphate (vitamin B(1)), pyridoxol phosphate (vitamin B(6)), and the nonmevalonate family of isoprenoid compounds recently discovered in bacteria and plant chloroplasts. Both 4 and 5 were synthesized from commercially available (-)-2,3-O-isopropylidene-D-threitol (10). The protected tetraol was converted to (-)-3,4-O-isopropylidene-5-triisopropylsilyl-1-deoxy-D-xylulose (14) in four steps. Treatment of 14 with acetic acid gave 4 in an overall yield of 69%. The corresponding 5-phosphate was obtained by protection the carbonyl group in 14, removal of the triisopropylsilyl moiety, and treatment of the resulting alcohol with trimethyl phosphite/TeCl(4), trimethylsilyl bromide, water, and HCl in successive steps to give 5 in 58% overall yield from 10.

Citations

Dec 19, 2000·Enzyme and Microbial Technology·F GiffhornS Freimund
Jul 7, 2005·Proceedings of the National Academy of Sciences of the United States of America·Hitoshi SakakibaraShinjiro Yamaguchi
Sep 30, 2004·Bioorganic & Medicinal Chemistry Letters·C Phaosiri, Philip J Proteau

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