78505-05-2

Upstream product

• 96689-27-9 (R)-1-Phenylsulfonyl-2-methyl-3-butene 
• 873-55-2 sodium benzenesulfonate 
• 94807-84-8 (S)-3-Methyl-4-phenylsulfanyl-butyric acid ethyl ester 
• 66261-30-1 (S)-4-(benzyloxy)-2-methylbutan-1-ol 
• 185681-33-8 (2S)-2-methyl-3-(p-methoxyphenyl)-1-phenylsulfonylpropane 
• 88408-99-5 (2S)-4-(benzyloxy)-1-(phenylsulfonyl)-2-methylbutane 
• 185681-34-9 methyl (3S)-3-methyl-4-phenylsulfonylbutanoate 
• 94807-93-9 (S)-3-methyl-4-phenylthio-1-butanol 
• 78548-66-0 S-(+)-3-methyl-4-phenylsulfonylbutanoic acid 
• 156714-06-6 (-)-(S)-4-bromo-3-methylbut-1-ene 
• 78505-03-0 2-methyl-3-chloropropyl phenyl sulfone 
• 13012-61-8 [(3-chloro-2-methylpropyl)sulfanyl]benzene 

Downstream Products

• 78505-06-3 (S)-4-Benzenesulfonyl-3,7-dimethyl-octan-1-ol 
• 219654-09-8 ((S)-4-Benzenesulfonyl-3-methyl-butoxy)-tert-butyl-diphenyl-silane 
• 87106-27-2 (S)-2-methyl-1-phenylsulfonylbutane 
• 219654-16-7 [(2R,3R)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxiranyl]-methanol 
• 1025839-70-6 (E)-(3S,8S)-4-Benzenesulfonyl-10-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3,7,8-trimethyl-dec-6-en-5-ol 
• 219654-13-4 (E)-(3S,8S)-4-Benzenesulfonyl-10-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3,7,8-trimethyl-dec-6-en-5-one 
• 219654-17-8 (E)-(3S,8S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3,7,8-trimethyl-dec-6-en-5-one 
• 219654-14-5 ((E)-(3R,8S)-10-Benzyloxy-3,7,8-trimethyl-5-methylene-dec-6-enyloxy)-tert-butyl-diphenyl-silane 
• 219654-15-6 (2E,8E)-(5S,10S)-12-Benzyloxy-5,9,10-trimethyl-7-methylene-dodeca-2,8-dien-1-ol 
• 219654-07-6 (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde 
• 185681-36-1 2-((3S,7R)-4-Benzenesulfonyl-3,7,11-trimethyl-dodecyloxy)-tetrahydro-pyran 
• 185681-37-2 (3S,7R)-4-Benzenesulfonyl-3,7,11-trimethyl-dodecan-1-ol 
• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 185681-35-0 (3S)-3-methyl-4-phenylsulfonylbutyl tetrahydropyranyl ether 

Relevant academic research and scientific papers

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.

Synthetic studies toward potent cytotoxic agents amphidinolides: Synthesis of the C1-C18 moiety of amphidinolides G, H and L

Stereoselective synthesis of the (8S, 9S, 11R, 16S)-C1-C18 segment 1 of amphidinolides G, H and L, bearing the unique trisubstituted 's-cis-1,3- diene' moiety (C(28(29))=C13-C14=C15), has been achieved for the first time following a highly efficient convergent strategy.

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.

SYNTHESIS OF DOLICHOL-TYPE (S)-HEXA- AND (S)-HEPTAPRENOLS

(R)-1-Phenylsulfonyl-2-methylbutan-4-ol has been used as starting material for the stepwise synthesis of the dolichol-related hexa- and heptaprenols (S)-3,7,11,15,19,23-hexymethyltetraicosa-6Z,10Z,14E,18E,22-pentaene1-ol and (S)-3,7,-11,15,19,23,27-heptamethyloctaicosa-6Z,10Z,14E,18E,22E,26-hexaen-1-ol.

A SATURATED ASYMMETRIC ISOPRENE SYNTHON SYNTHESIS, RESOLUTION AND ABSOLUTE CONFIGURATION

The unknown racemic 3-methyl-4-phenylsulfonylbutanoic acid (4) is synthesized by standard procedures.The acid is resolved into its enantiomers by alternating treatment with l- and d-ephedrine.The S-(+)-acid 4 is converted into R-(+)-dihydrocitronellol (7)