53730-41-9

Upstream product

• 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 
• 53730-39-5 (S)-(-)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid 

Downstream Products

• 119817-85-5 (S)-5-[2-[3,4-dihydro-2,5,7,8-tetramethyl-6-phenylmethoxy-2H-1-benzopyran-2-yl]-1-hydroxyethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 53713-37-4 (6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-yl)-acetic acid methyl ester 
• 59-02-9 Tocopherol 
• 119817-82-2 (S)-3-oxo-4-<3,4-dihydro-2,5,7,8-tetramethyl-6-benzyloxychroman-2-yl>butanoic acid methyl ester 

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.

2-(trimethyl-tridecenyl)-tetramethylchroman intermediates for vitamin E

6-Etherified hydroxy -2-(4',8',12'-trimethyl-5'-tridecenyl)-2,5,7,8-tetramethylchromans with an oxo or hydroxy substituent at the 2' position which may be substituted with an arylsulfonyl or a carboxyalkyl at the 3' position and containing a single or double bond at the 11 position, said chromans being intermediates for producing natural vitamin E.