122169-83-9

Upstream product

• 122079-41-8 (5S)-(D-menthyloxy)-2(5H)-furanone 
• 108-98-5 thiophenol 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 122079-45-2 (-)-(5R)-5-((-)-menthyl)oxy-2<5H>-furanone 

Downstream Products

• 76282-48-9 (R)-2-(oxiran-2-yl)ethan-1-ol 
• 139333-17-8 (S)-4-Chloro-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-4-phenylsulfanyl-dihydro-furan-2-one 
• 97719-35-2 (-)-(S)-2-phenylsulfanylbutane-1,4-diol 
• 97719-36-3 (R)-2-phenylthio-1,4-butanediol 
• 139333-18-9 (S)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-phenylsulfanyl-5H-furan-2-one 
• 139333-19-0 (1S,2S,5S,6R,7R)-6-Benzenesulfonyl-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 139333-16-7 (5S)-5-(d-Menthyloxy)-4-(phenylsulfonyl)-2(5H)-furanone 
• 139333-16-7 (5R)-5-(d-Menthyloxy)-4-(phenylsulfonyl)-2(5H)-furanone 
• 139333-20-3 (3S,3aR,7aS)-3a-Benzenesulfonyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5,6-dimethyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one 

Relevant academic research and scientific papers

Phenylsulfonyl-substituted 5-Alkoxy-2(5H)-furanones; a New Class of Highly Reactive Chiral Dienophies.

The synthesis of enantiomerically pure (5S)-5-(d-menthyloxy)-4-(phenylsulfonyl)-2(5H)-furanone (4) and the application of 4 as efficient dienophile in Diels-Alder reactions under mild conditions with enantioselectivities >98 percent e.e are described.

ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES. AN EFFICIENT SYNTHESIS OF (R)- AND (S)-3,4-EPOXY-1-BUTANOL

The synthesis of enantiomerically pure 5-menthyloxy-2(5H)-furanones is described as well as the diastereoselective 1,4-addition of thiols to these butenolides to yield new homochiral C4-synthons.Kinetic resolution of 5-methoxy-2(5H)-furanone, with an enantiomeric excess of 13percent, was achieved by cinchonidine catalysed thiophenol addition. The synthetic utility of the asymmetric thiol additions is illustrated in an efficient route to enantiomerically pure (R)- and (S)-3,4-epoxy-1-butanol.