1,3-Oxathiolane

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.

Preparation and occurrence

 * [[image:Apricitabine.svg|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-Methyl-4-propyl-1,3-oxathiane is a component of the flavor of passion fruit and other fruits.

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 A bulky derivative has been characterized by X-ray crystallography.