87441-49-4

Basic information

• Product Name: (-)-(1S)-2,2-dimethyl-1,3-dithian 1-oxide
• CAS NO: 87441-49-4
• Molecular Weight: 164.293
• Mol File: 87441-49-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (-)-(1S)-2,2-dimethyl-1,3-dithian 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1S)-2,2-dimethyl-1,3-dithian 1-oxide(87441-49-4)
• EPA Substance Registry System: (-)-(1S)-2,2-dimethyl-1,3-dithian 1-oxide(87441-49-4)

Safety Data

• Hazardous Substances Data: 87441-49-4(Hazardous Substances Data)

Upstream product

• 6007-22-3 2,2-dimethyl-1,3-dithiane 

Relevant articles and documents

Stereoselectivity of Prochiral Thioalkyl Groups in the Enzymatic Oxidation of Thioacetals by Fungi

Enzymatic oxidation of 2-substituted 1,3-dithians in cultures of a Helminthosporium species shows a stereo-preference for equatorial oxidation and for (1S)-monosulphoxide products.

Enantio and diastereoselectivity of cyclohexanone monooxygenase catalyzed oxidation of 1,3-dithioacetals

The asymmetric oxidation of 2-substituted dithianes, dithiolanes and oxathiolanes catalyzed by cyclohexanone monooxygenase (CMO) has been examined. The introduction of substituents at the C-2 causes a decrease of the e.e. with the exception of 2-benzoyl-1,3-dithiane monosulfoxide (90% e.e). With 2-monosubstituted dithioacetals CMO yields preferentially or exclusively the trans diastereoisomer. The binding of the 1,3-dithioacetals at the active site of the enzyme is not only controlled by the sterical hindrance of the substituents in position 2 but also by the configuration at C-2. The stereoselectivity of CMO has been compared with that reported for microsomal flavin and cytochrome P-450 monooxygenases.

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

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.