177568-10-4

Basic information

• Product Name: (2R,3R,4R)-2,4-dimethyl-5-(phenylthio)pentane-1,3-diol
• Synonyms: (2R,3R,4R)-2,4-dimethyl-5-(phenylthio)pentane-1,3-diol
• CAS NO: 177568-10-4
• Molecular Weight: 240.367
• Mol File: 177568-10-4.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-2,4-dimethyl-5-(phenylthio)pentane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-2,4-dimethyl-5-(phenylthio)pentane-1,3-diol(177568-10-4)
• EPA Substance Registry System: (2R,3R,4R)-2,4-dimethyl-5-(phenylthio)pentane-1,3-diol(177568-10-4)

Safety Data

• Hazardous Substances Data: 177568-10-4(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 177568-09-1 (2R,3S,4S)-3,5-dihydroxy-2,4-dimethylpentyl acetate 
• 127808-53-1 (2R,3s,4S)-3-[(tert-butyl-dimethylsilyl)oxy]-2,4-dimethylpentane-1,5-diol 
• 94842-97-4 (2SR,3SR,4RS)-2,4-dimethylpentane-1,3,5-triol 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 177420-68-7 (2R,4R)-2,4-dimethyl-1-phenylthio-hexane 
• 293744-11-3 ((2R,3R,4R)-5-Benzenesulfonyl-3-methoxy-2,4-dimethyl-oct-7-enyloxy)-triisopropyl-silane 
• 293744-08-8 ((2R,3R,4R)-5-Benzenesulfonyl-3-methoxy-2,4-dimethyl-pentyloxy)-triisopropyl-silane 
• 293744-07-7 Triisopropyl-((2R,3R,4R)-3-methoxy-2,4-dimethyl-5-phenylsulfanyl-pentyloxy)-silane 

Relevant articles and documents

Asymmetric synthesis of stigmatellin and crocacin C

The crystalline sulfone 18 (X-ray analysis), prepared from the monoacetate product [i.e., (+)-12; 98.2% ee] of the lipase PS-catalyzed acetylation of anti,anti-2,4-dimethyl-1,3,5-pentantriol (19a), has been elaborated either to crocacin C (10) or stigmatellin (1), thereby providing a convenient divergent access to these two natural antibiotics.

A convenient preparation of elements of the stereotriade

Enzyme-catalysed acetylation of either syn,syn- or anti,anti-2,4-dimethyl-1,3,5-pentane triol, easily obtained from a mixture of diastereomeric 3-hydroxy-2,4-dimethylglutaric acids, proceeds stereoselectively with preferential attack of the hydromethyl group linked to the R carbon atom of the starting triol, hence providing synthons useful for preparing compounds of the polypropionic pool.