185681-34-9

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 185681-33-8 (2S)-2-methyl-3-(p-methoxyphenyl)-1-phenylsulfonylpropane 
• 186581-53-3 diazomethane 
• 78548-66-0 S-(+)-3-methyl-4-phenylsulfonylbutanoic acid 

Downstream Products

• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 185681-35-0 (3S)-3-methyl-4-phenylsulfonylbutyl tetrahydropyranyl ether 
• 185681-37-2 (3S,7R)-4-Benzenesulfonyl-3,7,11-trimethyl-dodecan-1-ol 
• 185681-36-1 2-((3S,7R)-4-Benzenesulfonyl-3,7,11-trimethyl-dodecyloxy)-tetrahydro-pyran 
• 78505-05-2 (3S)-3-methyl-4-phenylsulfonylbutanol 

Relevant academic research and scientific papers

A synthesis of (2R,4'R,8'R)-α-tocopherol (vitamin E) side chain

Optically pore (3R,7R)-3,7,11-trimethyldodecan-1-ol (16), corresponding to the α-tocopherol side chain, was synthesized by the coupling reaction of a chiral isoprene unit (3S)-9 derived from an enzymatically hydrolyzed product (2S,3S)-2 and a ten-carbon alkylating reagent (R)-13 derived from (R)-(+)-pulegone.

Chemoenzymatic synthesis of (+)-α-polypodatetraene and methyl (5R,10R,13R)-labda-8-en-15-oate

The reported enzymatic resolution products {acetate of (1S,4aS,8aS)-1,2,3, 4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2- ethylene acetal} (8aS)-5 (>99% ee)] and [(1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a- decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-4 (98% ee) were converted to (+)-α-polypodatetraene (1) and methyl (5R,10R,13R)-labda-8-en-15-oate (2), respectively. For the synthesis of (5R,10R,13R)-2, chiral isoprene congener (3S)-26 corresponding to the right part of 2 was synthesized based on the lipase-assisted resolution of (±)-2-methyl-3- (p-methoxyphenyl)propanol (17).

Enantioselective synthesis of (2R,4'R,8'R)-α-tocopherol (Vitamin E) based on enzymatic function

Syntheses of (S)-chroman-2-carboxaldehyde congener 1 and (S)-chiral isoprene unit 3 were achieved based on the enzymatic acetylation of (±)- chroman-2-methanol 6 and (±)-(2,3)-anti-2-methyl-3-(p-methoxyphenyl)-1,3- propane diol 12, respectively. Synthesis of the side-chain part corresponding to (3R,7R)-3,7,11-trimethyldodecan-1-ol 27 was achieved by the coupling reaction of (S)-3 and (R)-3,7-dimethyloctyl iodide 4. The Wittig reaction of (3R,7R)-phosphonium salt 2 derived from (3R,7R)-27 and (S)-1 gave the olefin 28 which was subjected to catalytic hydrogenation to afford (2R,4'R,8'R)-α- tocopherol.