Welcome to LookChem.com Sign In|Join Free

Article Doi

Structure and Absolute Stereochemistry of Thioacetal Sulphoxides Obtained by Fungal Metabolism of 2 Alkyl-1,3-Dithianes

DOI: 10.1039/P19850001547

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1547 - 1552 (1985)

Update date:2022-07-29

Topics:

Authors:

Auret, Barbara J.Auret, Barbara J.

Boyd, Derek R.Boyd, Derek R.

Cassidy, E. SallyCassidy, E. Sally

Hamilton, RobertHamilton, Robert

Turley, FionaTurley, Fiona

Drake, Alex F.Drake, Alex F.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19850001547

Monosulphoxide metabolites of 2-methyl-, 2-t-butyl-, 2,2-dimethyl-, and 2-methyl-2-t-butyl-1,3-dithiane have been isolated after addition of the thioacetals to growing cultures of the fungi Aspergillus foetidus, Mortierella isabellina and a Helminthosporium species.The optical yields of the chiral monosulphoxide metabolites (0-72percent) were determined by n.m.r. analysis in (-)-phenyl- or 1-(+)-9-anthryl-2,2,2-trifluoroethanol-CDCl3 solvent mixtures.The signs of Cotton effects obtained from c.d. spectra have been used to assign the absolute stereochemistry of the chiral thioacetal sulphoxides.Optically pure samples 2,2-dimethyl-1,3-dithiane 1-oxide, cis-2-methyl-1,3-dithiane 1-oxide, and trans-2-methyl-1,3-dithiane 1-oxide, have been obtained by a chemical resolution method which provides confirmation of optical yields and absolute stereochemistry.The fungal metabolism results indicate that the mono-oxygenase enzymes can stereodifferentiate between prochiral (diastereotopic) Ione pairs on a sulphur atom and also between prochiral (enantiotopic) thioalkyl substituents on a carbon atom during the formation of monosulphoxides.

View More

Products guided by the article

Product name:(R)-2,2-dimethyl-1,3-dithiane-1-oxide

Cas No:619326-29-3

619326-29-3

R&D Labs maybe for 619326-29-3

Relevant to this article

Hot Product