112449-81-7

Upstream product

• 112449-84-0 (2RS,3RS,4RS)-2,4-Dimethyl-3-hydroxy-4-phenylsulfanylhexane-1,3-diol 
• 96-17-3 2-Methylbutyraldehyde 
• 98793-42-1 2-methyl-2-(phenylsulfenyl)butanal 
• 53282-51-2 (Z)-2-Methyl-1-(trimethylsiloxy)-1-butene 
• 112449-84-0 (2RS,3SR,4SR)-2,4-Dimethyl-3-hydroxy-4-phenylsulfanylhexane-1,3-diol 
• 112449-95-3 (2RS,3RS,4RS)-2,6-Dimethylphenyl 2,4-dimethyl-3-hydroxy-4-phenylsulfanylhexanoate 

Relevant academic research and scientific papers

Stereochemical control in the synthesis of tetrahydrofurans by cyclisation of diols with [1,2]phenylsulfanyl migration

Acid catalysed rearrangement of a series of 4-PhS-1,3-diols with toluene-p-sulfonic acid in benzene gives stereospecifically substituted 3-PhS-tetrahydrofurans in excellent yield via a [1,2]-SPh shift. We comment on the structural variation at both the migration origin and terminus on the outcome of the title reaction and define its limits.

Kinetic and thermodynamic control in the stereospecific synthesis of cyclic ethers via phenylsulfanyl (PhS) migration

The factors controlling the stereospecific cyclisation of 1,3-diols with PhS migration to give THFs rather than oxetanes are reassessed in the light of evidence that these reactions are under thermodynamic control. Rearrangement of cyclic sulfites gives the nearest approach to kinetic control.

STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF TETRAHYDROFURANS BY CYCLISATION OF DIOLS WITH PHENYLTHIO MIGRATION

Cyclisation of diols with PhS migration leads to tetrahydrofurans by inversion at both the migration origin and terminus.Cyclisation to a secondary migration terminus is controlled by stereochemical factors.

SYNTHESIS OF COMMPOUNDS WITH 1,4-RELATED CHIRAL CENTRES BY PHENYLTHIO MIGRATION: SYN AND ANTI-E-2,4-DIMETHYLHEX-3-ENE-1,5-DIOL

The aldol product from an α-PhS aldehyde, formed with high Cram and anti (aldol) selectivity, was transformed by PhS migration into the syn title compound: the anti compound was made by a Claisen-Ireland rearrangement.