188709-39-9

Upstream product

• 188709-37-7 tert-butyl (-)-(S_S)-3-oxo-4-p-tolylsulfinyl-butanoate 
• 1694-31-1 tert-butyl acetoacetate 
• 91796-57-5 4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 91796-57-5 (1S,2R,5S,R_S)-(+)-Menthyl toluene-p-sulfinate 

Downstream Products

• 188709-46-8 tert-butyl (-)-(3R,S_S)-3-tert-butyldimethylsilyloxy-4-p-tolylsulfinyl-butanoate 
• 244217-17-2 tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate 

Relevant academic research and scientific papers

First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1-C13 Fragment of Nystatin A1

A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin A1 is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an α-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synα,β-(R,S)-dihydroxy aldehyde.

Enantioselective synthesis of haminol-1, an alarm pheromone of a Mediterranean mollusc

The first enantioselective synthesis of (-)-(R)-haminol-1 is described in this paper. The chiral part of the molecule was prepared by reduction of an optically active β-ketosulfoxide. The all-trans trienic part was stereoselectively synthesized via reductive elimination of a 1,6-dibenzoate-2,4-diene with sodium amalgam.