115205-40-8

Upstream product

• 115205-37-3 1-(Methoxy-phenylsulfanyl-methyl)-cyclopentanol 
• 155091-53-5 1-(diacetoxymethyl)-1-(phenylsulfenyl)cyclopentane 
• 73880-63-4 (+/-)_S-cyclopentylidene(phenylsulfinyl)methane 
• 13865-50-4 methoxymethyl phenyl sulfide 

Downstream Products

• 138649-96-4 (4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclopentyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one 
• 174784-04-4 Ethyl 3-hydroxy-3-[1'-(phenylsulfanyl)cyclopentyl]propanedithioate 
• 179806-59-8 4-hydroxy-4-(1-(phenylthio)cyclopentyl)butan-2-one 
• 711028-37-4 (E)-4-(1-Phenylsulfanyl-cyclopentyl)-but-3-en-2-one 
• 133030-72-5 (1RS,2RS)-3-(t-butyldiphenylsiloxy)-1-(cyclopent-1-enyl)-2-methylpropyl phenyl sulphoxide 
• 133030-63-4 (1RS,2RS)-3-(t-butyldiphenylsiloxy)-2-methyl-1-<1-(phenylthio)cyclopentyl>propan-1-ol 
• 133030-68-9 (1'RS,2'SR)-1-<3'-(t-butyldiphenylsiloxy)-2'-methyl-1'-(phenylthio)propyl>cyclopentene 
• 133030-73-6 (1RS,2'SR)-(E)-2-<3'-(t-butyldiphenylsiloxy)-2'-methylpropylidene>cyclopentanol 
• 120749-37-3 (1RS,2RS)-2-methyl-1-<1-(phenylthio)cyclopentyl>propane-1,3-diol 
• 133030-51-0 (3RS,4SR)-3-methyl-4-(phenylthio)-1-oxaspiro<4.4>nonan-2-one 
• 120749-38-4 (3RS,4SR)-3-methyl-4-phenylthio-1-oxaspiro<4.4>nonane 
• 138649-99-7 (2S,3S)-3-hydroxy-2-methyl-3-(1-phenylsulfanylcyclopentyl)propylamine 
• 138649-99-7 (1R,2S)-3-Amino-2-methyl-1-(1-phenylsulfanyl-cyclopentyl)-propan-1-ol 
• 138650-00-7 (2S,3S)-3-hydroxy-2-methyl-3-(1-phenylsulfanylcyclopentyl)propyl-N-tosylamide 

Relevant academic research and scientific papers

Do the electronic effects of sulfur indeed control the π-selectivity of γ-sulfenyl enones? An investigation

The electronic effects of sulfur in γ-sulfenyl enones are not transmitted to the carbonyl carbon through the π bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising

The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1,3-diols

A solution of 2-methyl-3-[1-(phenylsulfanyl)cyclohexyl]propane-1,3-diol 1 in toluene treated with triphenyl-phosphine, Ziram 2 and DEAD, gave 3-methyl-2-[1-(phenylsulfanyl)cyclohexyl]oxetane 3 in 85% yield. A mechanistic study has been undertaken, optimal conditions have been found and the range of substrates for which the reaction is useful has been explored. We include the results of an X-ray study which shows that compound 33 (the oxidation product of diol 1) is a sulfone rather than a sulfoxide as previously reported.

Additive Pummerer reactions of vinylic sulfoxides. Synthesis of γ-hydroxy-α,β-unsaturated esters, α-hydroxyketones, and 2-phenylsulfenyl aldehydes and primary alcohols

Treatment of β-monosubstituted vinylic sulfoxides 1 with trifluoroacetic anhydride in dichloromethane gave excellent yields of 1,2-bis(trifluoroacetoxy)thioethers 6. Mildly basic methanolysis of 2-alkyl-substituted 6 gave α-hydroxyaldehydes 11 as monomer-dimer mixtures; similar treatment of the 2-aryl analogues afforded aryl (hydroxymethyl) ketones 12. Compounds 11 underwent Wittig reactions with methoxycarbonylmethylenetriphenylphosphorane to give high yields of γ-hydroxy-α,β-unsaturated esters 13, predominantly as the E-isomers. β-Monosubstituted vinylic sulfoxides 1 possessing a β-aryl group, and β-disubstituted vinylic sulfoxides 3 reacted with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride to give 2-(phenylsulfenyl) acylals 14. These gave 2-phenylsulfenyl aldehydes 15 upon basic methanolysis, and the corresponding primary alcohols 16 on reduction with sodium borohydride. Reaction of both geometric isomers of enantiomerically pure vinylic sulfoxide 1o with TFAA gave racemic 6o as a mixture of diastereomers. Reaction of optically pure (E)- and (Z)-1p with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride gave acylal 19 in 10.5 and 23% e.e., respectively.