195988-78-4

Basic information

• Product Name: (S)-4-Benzenesulfonyl-tridecan-2-ol
• Synonyms: (S)-4-Benzenesulfonyl-tridecan-2-ol
• CAS NO: 195988-78-4
• Molecular Weight: 340.527
• Mol File: 195988-78-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-4-Benzenesulfonyl-tridecan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Benzenesulfonyl-tridecan-2-ol(195988-78-4)
• EPA Substance Registry System: (S)-4-Benzenesulfonyl-tridecan-2-ol(195988-78-4)

Safety Data

• Hazardous Substances Data: 195988-78-4(Hazardous Substances Data)

Upstream product

• 24731-39-3 4-(phenylsulfonyl)butan-2-one 
• 4282-42-2 1-iodononane 
• 148118-28-9 (3S)-1-phenylsulphonyl-3-hydroxybutane 

Downstream Products

• 1653-31-2 (S)-(+)-tridecan-2-ol 

Relevant articles and documents

Synthesis of enantiomerically pure (1R,2R)- and (1S,2S)-2-alkyl-1-phenylsulfonylcyclopropanes using Bakers' yeast

Reduction of the ketone 1 with Bakers' yeast gives the alcohol (R)-2 with high enantiomeric excess, and this upon subsequent epoxidation and alkylation with Grignard reagents provides the alcohols (S)-4 without racemisation. Tosylation of the alcohols (S)-4 under common conditions yields the tosylates (toluene-p-sulfonates) (S)-5, whilst under Mitsunobu conditions inversion of configuration takes place giving the tosylates (R)-5. Subsequent treatment of the tosylates (S)-5 and (R)-5 with lithium diisopropylamide leads to cyclization affording the enantiomerically pure cyclopropanes (S,S)-6 and (R,R)-6 in high yields, respectively. The diastereoisomeric alcohol (S)-4f, obtained by methylation of the alcohol (S)-4e, can also be converted into the single stereoisomer (R,R)-6f in enantiomerically pure form.