59965-06-9

Upstream product

• 59965-21-8 (S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol p-toluenesulfonate 
• 58846-71-2 (-)-(S)-methyl(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetate 
• 58846-72-3 (2S)-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid methyl ester 
• 53730-39-5 (S)-(-)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid 
• 2385-77-5 (R)-Citronellal 
• 76832-12-7 (6R)-(E)-6,10-dimethyl-3,9-undecadien-2-one 
• 114341-71-8 (4R,8R)-1-Bromo-4,8,12-trimethyltridecane 
• 114341-58-1 rac-2-Chloro-3,4-dihydro-2,5,7,8-tetramethyl-6-(phenylmethoxy)-2H-1-benzopyran 
• 53713-30-7 6-benzyloxy-2-methoxy-2,5,7,8-tetramethylchroman-2-ol 
• 1228359-93-0 C₃₇H₅₆O₄ 
• 119776-03-3 <2S-(4R,5E,8R)>-1-<2,5,7,8-tetramethyl-6-benzyloxychroman-2-yl>-4,8,12-trimethyl-3-phenylsulfonyltrideca-2,5,11-triene 
• 119775-99-4 (S)-1-<3,4-dihydro-2,5,7,8-tetramethyl-6-benzyloxychroman-2-yl>-3'-phenylsulfonyl-2-propanone 
• 119789-58-1 methyl (2R,6R,3E)-6,10-dimethyl-3,9-undecadien-2-yl carbonate 
• 162810-67-5 (2S,4'R,8'R)-2',5',11'-α-tocotrienol benzyl ether 

Downstream Products

• 59-02-9 Tocopherol 
• 58-95-7 RRR-α-tocopheryl acetate 

Relevant academic research and scientific papers

Highly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons: Via palladium catalysis

Aryl carboxylic acids are among the most abundant substrates in chemical synthesis and represent a perfect example of a traceless directing group that is central to many processes in the preparation of pharmaceuticals, natural products and polymers. Herein, we describe a highly selective method for the direct step-down reduction of carboxylic acids to arenes, proceeding via well-defined Pd(0)/(ii) catalytic cycle. The method shows a remarkably broad substrate scope, enabling to direct the classical acyl reduction towards selective decarbonylation by a redox-neutral mechanism. The utility of this reaction is highlighted in the direct defunctionalization of pharmaceuticals and natural products, and further emphasized in a range of traceless processes using removable carboxylic acids under mild, redox-neutral conditions orthogonal to protodecarboxylation. Extensive DFT computations were conducted to demonstrate preferred selectivity for the reversible oxidative addition and indicated that a versatile hydrogen atom transfer (HAT) pathway is operable.

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.