112449-95-3

Upstream product

• 51233-80-8 2,6-dimethylphenyl propionate 
• 98793-42-1 2-methyl-2-(phenylsulfenyl)butanal 
• 53282-51-2 (Z)-2-Methyl-1-(trimethylsiloxy)-1-butene 
• 96-17-3 2-Methylbutyraldehyde 

Downstream Products

• 112449-84-0 (2RS,3SR,4SR)-2,4-Dimethyl-3-hydroxy-4-phenylsulfanylhexane-1,3-diol 
• 112449-81-7 (2RS,3SR,4RS)-2,4-Dimethyl-2-ethyl-3-phenylsulfanyltetrahydrofuran 
• 112449-94-2 (2S,3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-4-phenylsulfanyl-hexan-3-ol 
• 112449-92-0 (E)-(2S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-3-en-2-ol 

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.

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.