1,3-Oxathiolane Explained

1,3-Oxathiolane is an organosulfur compound with the formula . It is a saturated five-membered heterocycle with non-adjacent S and O atoms. It is the parent of numerous derivatives. The parent compound is of little practical value, but there is some biotechnological interest in derivatives where one or more H atoms are replaced by other substituents.^[1]

Preparation and occurrence

thumb|left|Apricitabine, a drug candidate containing a 1,3-oxathiane, is a nucleoside reverse transcriptase inhibitor.The compound is prepared by condensation of mercaptoethanol with formaldehyde, as typical for synthesis of thioacetals.^[2]

2-Methyl-4-propyl-1,3-oxathiane is a component of the flavor of passion fruit and other fruits.^[3]

1,2-Oxathiolane

In contrast to the well-developed area of 1,3-oxathiolanes, 1,2-oxathiolane and its derivatives are not prevalent in the literature. The parent compound, which is derived from 3-mercaptopropanol, has been detected in solution^[4] A bulky derivative has been characterized by X-ray crystallography.^[5]

References

1. Web site: 1,3-Oxathiolane .
2. 10.1021/ja01111a029 . Studies in Organic Sulfur Compounds. VI. Cyclic Ethylene and Trimethylene Hemithioketals . 1953 . Djerassi . Carl . Gorman . Marvin . Journal of the American Chemical Society . 75 . 15 . 3704–3708 .
3. 10.1016/j.foodres.2015.09.007 . Profiling of passion fruit volatiles: An effective tool to discriminate between species and varieties . 2015 . Porto-Figueira . Priscilla . Freitas . Ana . Cruz . Catarina J. . Figueira . José . Câmara . José S. . Food Research International . 77 . 408–418 .
4. 10.1039/C39810000741 . 1,2-Oxathiolan, a simple sultene . 1981 . Davis . Anthony P. . Whitham . Gordon H. . Journal of the Chemical Society, Chemical Communications . 15 . 741 .
5. 10.1021/ja00546a047 . Rearrangement of penicillin sulfoxides in base. Penicillin-derived sulfines . 1980 . Baldwin . Jack E. . Herchen . Stephen R. . Schulz . Guenter . Falshaw . Christopher P. . King . Trevor J. . Journal of the American Chemical Society . 102 . 26 . 7815–7816 .