55776-46-0

Upstream product

• 130826-84-5 (2E)-acetic acid 6-bromo-7-hydroxy-3,7-dimethyl-oct-2-enyl ester 
• 100-39-0 benzyl bromide 
• 52188-73-5 geranyl benzyl ether 
• 106-24-1 Geraniol 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 40036-54-2 (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 

Downstream Products

• 68690-80-2 (E)-6,7-dihydroxy-3,7-dimethyl-2-octenyl benzyl ether 
• 68690-78-8 (2E)-1-benzyloxy-6-hydroxy-3,7-dimethyl-2,7-octadiene 
• 32989-52-9 (E)-4-methyl-6-(phenylmethoxy)-4-hexenal 
• 862877-65-4 (-)-(2'S,1R,4E)-6-benzyloxy-4-methyl-1-(2'-methyloxiranyl)-hex-4-en-1-ol 
• 862877-68-7 (-)-(2S,6E)-8-benzyloxy-2-hydroxy-2,6-dimethyloct-6-en-3-one 
• 862877-73-4 (+)-(2S,3R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2,3-dihydroxy-2,6-dimethyl-oct-6-enyl ester 
• 862877-74-5 (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester 
• 862877-69-8 (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester 
• 862877-71-2 (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2,6-dimethyl-3-oxo-2-trimethylsilanyloxy-oct-6-enyl ester 
• 121926-78-1 (2E,6E,10E)-1-benzyloxy-7-formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraene 
• 121926-82-7 (E)-2-[(E)-6-Benzyloxy-4-methyl-hex-4-en-(Z)-ylidene]-6,10-dimethyl-undeca-5,9-dien-1-ol 
• 146905-11-5 (E)-2-[(E)-6-Benzyloxy-4-methyl-hex-4-en-(Z)-ylidene]-6,10-dimethyl-undeca-5,9-dienenitrile 
• 98066-00-3 (E)-4-methyl-6-(phenylmethoxy)-4-hexen-1-ol 
• 118512-38-2 (2E,6,7-anti)-1-benzyloxy-6,7-dihydroxy-3,7-dimethyl-2-octene 

Relevant academic research and scientific papers

New methodology for the conversion of epoxides to alkenes

Epoxides have been transformed in good yields to alkenes by a process involving (i) ring-opening of the epoxide with 2-mercaptobenzothiazole, (ii) oxidation of the derived ss-hydroxy thioethers to the corresponding sulfones, and (iii) thermal or base-promoted fragmentation of these sulfones to alkenes. The stereochemistry of the starting epoxide is transfer-red faithfully to the alkene product, because of the SN2 epoxide ring-opening reactions and the antiperiplanar SO2 elimination reaction of the ss- alkoxysulfinate intermediates. This methodology may form the basis of a new protecting group strategy for alkenes.

Studies on the synthesis of DNA-damaging part of leinamycin: Regioselectivity in Ti(OiPr)4 mediated opening of hydroxy epoxides with carboxylic acids

The preparation of the key intermediate in the synthesis of the DNA damaging fragment of the anticancer antibiotic leinamycin starting from geraniol is described. The synthetic sequence involves the building of a quaternary asymmetric center through kinetic resolution through Sharpless epoxidation followed by the regioselective opening of the resultant enantiomerically pure hydroxyepoxide and intramolecular Wittig-Horner olefination.

A practical synthesis of (-)-kazusamycin A (revised)

We describe herein a stereo-controlled and practical synthesis of three key building blocks, namely Segment AB′, Segment D, and Segment E′ needed for the total synthesis of (-)-kazusamycin A.

Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male Danaus chrysippus (African Monarch)

The synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (1), which was isolated from the hairpencils of male Danaus chrysippus (African Monarch), was investigated. The key step of the sequence involves asymmetric desymmetrization of the 1,3-propanediol 7 with

Tetracyanoethylene-hydrogen peroxide, a mild epoxidation system of olefins

A reagent combination system, tetracyanoethylene-30% hydrogen peroxide, was found to epoxidize olefins efficiently in acetonitrile at room temperature in a stereospecific manner with retention of the configuration of the double bond.

Z-selective formation of trisubstituted α,β-unsaturated nitrile by the Horner-Emmons reaction

Conditions which allow the Horner-Emmons reaction of phosphononitrile to proceed Z-selectively were clarified. The generality and usefulness of the procedure were demonstrated by an application to a stereoselective synthesis of plaunotol (9).

Ethyl Cyanoformate/Hydrogen Peroxide and Related Combination Systems, Novel Epoxidizing Systems of Olefins

A combination system of ethyl cyanoformate and hydrogen peroxide was found to epoxidize olefins in a stereospecific manner at room temperature.Asymmetric epoxidation was observed with menthyl cyanoformate/hydrogen peroxide system.

CONVENIENT SYNTHESIS OF CHIRAL EPOXYISOPRENOIDS BY YEAST REDUCTION

The terminal double bond of acyclic isoprenoids was converted into chiral epoxide in high optical yield by using asymmetric reduction of α-ketol with baker's yeast.

CONVENIENT SYNTHETIC ROUTE TO (+)-FARANAL AND (+)-13-NORFARANAL; THE TRAIL PHEROMONE OF PHARAOH'S ANT AND ITS CONGENER

(+)-Faranal 1a, the trail pheromone of Pharaoh's ant, and its congener, (+)-13-norfaranal 1b were synthetized from chiral building block 4 employing diastereoselective carbon-carbon bond formation.The application of crude pig liver esterase enzyme for the

Highly Stereoselective Total Synthesis of Plaunotol

Highly stereoselective total synthesis of plaunotol has been achieved by the application of the (Z)-stereoselective direct Wittig olefination to α-alkoxy ketones having geranylacetone skeleton.