119817-85-5

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 53730-41-9 (S)-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid 
• 53730-39-5 (S)-(-)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid 
• 58846-72-3 (2S)-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid methyl ester 
• 58846-71-2 (-)-(S)-methyl(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetate 

Downstream Products

• 119817-82-2 (S)-3-oxo-4-<3,4-dihydro-2,5,7,8-tetramethyl-6-benzyloxychroman-2-yl>butanoic acid methyl ester 
• 59-02-9 Tocopherol 

Relevant academic research and scientific papers

A MICROBIAL LIPASE BASED STEREOSELECTIVE SYNTHESIS OF (d)-α-TOCOPHEROL FROM (R)-CITRONELLAL AND (S)-(6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-YL)ACETIC ACID

A new sythesis of natural vitamin E (2R,4'R,8'R)-α-tocopherol) based on (R)-citronellal and (S)-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid is described.The citronellal is elaborated into an optically pure C13 allylic carbonate using a lipase catalyzed kinetic resolution to control the new chiral center.Palladium catalyzed coupling of the C13 carbonate with either a β-ketoester or β-ketosulphone derived from the chromanylacetic completes the assembly of the α-tocopherol skeleton.Appropriate functional group modifications are used to complete the synthesis.