Sharma, KamleshLaurens, Johannes B.Pilcher, Lynne A.2017-02-282017-02-282009Kamlesh Sharma , J. B. Laurens & Lynne A. Pilcher (2009) Stereoselective Synthesis of the Urinary Metabolite N-Acetyl-S-(3,4-dihydroxybutyl)cysteine, Synthetic Communications, 39:8, 1415-1424, DOI: 10.1080/00397910802527763.0039-7911 (print)1532-2432 (online)10.1080/00397910802527763http://hdl.handle.net/2263/59199On exposure to the potential carcinogen 1,3-butadiene, the major urinary metabolite in humans is N-acetyl-S-(3,4-dihydroxybutyl)cysteine. A novel, stereoselective synthesis of this cysteine–butadiene metabolite has been developed that is suitable for the production of either diastereomer for use in occupational exposure analysis. L-Cysteine and 4-bromo-1-butene are coupled via an SN2 reaction to give the core structure. A Sharpless asymmetric dihydroxylation using the dihydroquinidine (DHQD) ligand provided the terminal 1,2-diol with the 3-hydroxyl group in the R configuration. Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 to view the free supplemental resourceen© Taylor & Francis Group, LLC. This is an electronic version of an article published in Synthetic Communications, vol. 39, no. 8, pp. 1415-1424, 2009. doi : 10.1080/00397910802527763. Synthetic Communications is available online at : http://www.tandfonline.comloi/lsyc20.DihydroxylationStereoselective synthesisUrinary metaboliteN-acetyl-S-(3,4-dihydroxybutyl)cysteineCysteine–butadiene metabolitePostprint Article