1,3-Oxathiolane
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.
Preparation and occurrence
The compound is prepared by condensation of mercaptoethanol with formaldehyde, as typical for synthesis of thioacetals.Derivatives
2-Methyl-4-propyl-1,3-oxathiane is a component of the flavor of passion fruit and other fruits.Apricitabine, a drug candidate containing a 1,3-oxathiane, is a nucleoside [reverse transcriptase inhibitor].
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 solutionA bulky derivative has been characterized by X-ray crystallography.