1,3-Oxathiolane

1,3-Oxathiolane

1,3-Oxathiolane

Chemical compound

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]

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Preparation and occurrence

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