77372-64-6

Upstream product

• 84230-94-4 (3S,4S)-4-Hydroxy-tetrahydro-thiopyran-3-carboxylic acid methyl ester 
• 4160-61-6 3-methoxycarbonyltetrahydropyran-4-one 
• 86421-21-8 (4RS,6S,7S)-Serricornin 
• 84230-94-4 (3R,4S)-Tetrahydro-4-hydroxy-2H-thiopyran-3-carbonsaeure-methylester 
• 90276-94-1 (3R,4S)-Tetrahydro-4-hydroxy-2H-thiopyran-3-carbonsaeure 
• 78433-62-2 (4RS,6S,7S)-7-t-butyldimethylsilyloxy-4,6-dimethyl-3-nonanone 
• 84230-97-7 (2R,3S)-3-(tert-Butyldimethylsiloxy)-1-iod-2-methylpentan 
• 84230-95-5 (2R,3S)-3-(tert-Butyldimethylsiloxy)-2-methylpentansaeure-methylester 
• 60665-94-3 (2R,3S)-3-Hydroxy-2-methylpentansaeure-methylester 
• 84230-96-6 (2S,3S)-3-<(tertbutyl)dimethylsilyloxy>-2-methylpentan-1-ol 

Relevant academic research and scientific papers

Stereoselective Synthesis of Alcohols, XVIII. - Synthesis of (3S,4S)-4-Methyl-3-heptanol and of (5S,6S)-Anhydroserricornin

Yeast reduction of methyl tetrahydro-4-oxo-2H-thiopyran-3-carboxylate (5) led to the β-hydroxy ester 6 of 98percent diastereomeric and ca. 85percent enantiomeric purity. 6 was converted into enantiomerically pure anti-4-methyl-3-heptanol (4) and via the key intermediate 11 into enantiomerically pure anhydroserricornin (3).

SYNTHESIS OF 6S,7S-ANHYDRO-SERRICORNINE.

Diastereoselective and enantioselective reduction of the β-ketoester 3 by yeast to 4 provided the chiral starting material for a synthesis of 4RS,6S,7S-serricornine, having the same configuration as the natural product.This material was converted into optically active and diastereomerically pure 6S,7S-anhydro-serricornine (2).