1,3-Oxathiolane

1,3-Oxathiolan.svg 125px 1,3-Oxathiolane 2094-97-5 58602 65092 1S/C3H6OS/c1-2-5-3-4-1/h1-3H2 WJJSZTJGFCFNKI-UHFFFAOYSA-N C1CSCO1 3 6 1 1 colorless liquid 1.1779 g/cm3 127-129 1,3-Oxathiolane is an organosulfur compound with the formula (CH2)3OS. 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.1,3-Oxathiolane https://pubchem.ncbi.nlm.nih.gov/compound/1_3-Oxathiolane Preparation and occurrence The compound is prepared by condensation of mercaptoethanol with formaldehyde, as typical for synthesis of thioacetals.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 Derivatives 2-Methyl-4-propyl-1,3-oxathiane is a component of the flavor of passion fruit and other fruits.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 Apricitabine, a drug candidate containing a 1,3-oxathiane, is a nucleoside reverse transcriptase inhibitor. thumb|left|Chemical structure of apricitabine 1,2-Oxathiolane thumb|right|120px|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 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 A bulky derivative has been characterized by X-ray crystallography.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 References