130583-95-8

Upstream product

• 20548-02-1 (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 60046-49-3 (6R)-levodione 

Downstream Products

• 152187-06-9 (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene 
• 130584-04-2 (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((Z)-5-hydroxy-3-methyl-pent-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol 
• 444122-12-7 [(4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-cyclohex-(Z)-ylidene]-hydrazine 
• 444122-13-8 tert-butyldimethylsilyl (R)-4-iodo-3,5,5-trimethylcyclohex-3-en-1-yl ether 
• 214335-71-4 (-)-[(S)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-enyl]methanol 
• 83021-07-2 (S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one 
• 473758-71-3 (R)-4-[(1E,3E,7E)-9-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,7-trien-5-ynyl]-3,5,5-trimethyl-cyclohex-3-enol 
• 473758-68-8 (R)-4-[(1E,3E,5Z,7E)-9-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enol 
• 473758-70-2 3-[N⁶-biotinyl-N²-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol 
• 473758-69-9 2-tert-butoxycarbonylamino-6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 4-[9-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-3,5,5-trimethyl-cyclohex-3-enyl ester 
• 444122-15-0 (S)-4-[(E)-but-1-en-3-ynyl]-3,5,5-trimethylcyclohex-3-en-1-ol 
• 444122-16-1 (R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol 
• 444122-14-9 (S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether 
• 245504-00-1 [(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]acetaldehyde 

Relevant academic research and scientific papers

Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins

The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-O]-all trans-retinol chloroacetate is described. These biotinylated retinoids are instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Horner-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings.

Stereocontrolled synthesis and configurational assignment of (R)-all-trans-11,12-dihydro-3-hydroxyretinol

The synthesis of (R)-all-trans-11,12-dihydro-3-hydroxyretinol and putative metabolites of the side-chain functional group has been achieved in a stereocontrolled manner via the Suzuki-Hiyama cross-coupling reaction of an enantiopure (hydroxycyclohexenyl)alkenyliodide and non-conjugated pinacolboranedienoate, which allowed the absolute configuration of this natural product to be confirmed.

Synthesis of labile all-trans-7,8,7′,8′-bis-acetylenic carotenoids by bi-directional Horner-Wadsworth-Emmons condensation

A new stereoselective synthesis of the C40-bis-acetylenic carotenoids all-trans-(3R,3′R)-alloxanthin and all-trans-3,4,7,8,3′,4′,7′,8′-octadehydro-β,β-carotene, both compounds featuring a stereochemically labile C7-C10 enyne, based on a bi-directional Horner-Wadsworth-Emmons (HWE) reaction of a C15-phosphonate and a central C10-dialdehyde, is reported. The triene unit of the latter fragment was synthesized using the acyclic metathesis/dimerization reaction.

Total synthesis of naturally configured pyrrhoxanthin, a carotenoid butenolide from plankton

A carotenoid from the chemical kitchen: Two sequential Stille couplings of an unsymmetric distannane building block with a bromoolefin and a bromoalkyne terminated a highly convergent synthesis of the title compound, pyrrhoxanthin (see scheme).

Total synthesis of peridinin and related C37-norcarotenoid butenolides

As an extension of our synthesis of symmetrical carotenoids, the preparation of the highly functionalized C37-norcarotenoid butenolide peridinin (1), its 6′-epi- and 11′Z stereoisomers has been completed. Featuring a central dihalogenated Csub

Synthesis of symmetrical carotenoids by a two-fold Stille reaction

β-Carotene 1 and (3R,3′R)-zeaxanthin 2 have been stereoselectively prepared in a highly convergent fashion by a 2-fold Stille cross-coupling reaction. The C12-pentaenylbis-stannane 8 is the central "lynchpin" that connects two units of the terminal C14-iodides 9 and 17 to afford 1 and 2, respectively.

First total synthesis of crassostreaxanthin B

The first total synthesis of crassostreaxanthin B 1 was accomplished via the tetrasubstituted olefinic compound 5, prepared by stereoselective rearrangement of epoxides 3a,b using a Lewis acid.

First Total Synthesis of (+/-)-Peridinin, (+/-)-Pyrrhoxanthin and the Optically Active Peridinin

The first total synthesis of peridinin 1 and pyrrhoxanthin 2 has been accomplished via the reaction of the C15-epoxy formyl ester 21 with the C22-allenic sulfone 28 or the C22-acetylenic sulfone 39.A synthesis of the optically active peridinin has also be

Synthesis of optically active cyclohexanone analogs of the plant hormone abscisic acid

The abscisic acid analogs (-)-(4R,5R)-, (+)-(4S,5S)-, and (-)-(4S,5R)-4(1E,3Z)-4-(4-carboxy-3-methyl-1,3-butadienyl)-4-hydroxy-3,3,5-trimethylcyclohexanones (dihydroabscisic acids), and (-)-(4S,5R)-, (+)-(4R,5S)-, and (-)-(4R,5R)-4(Z)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanones were synthesized from a common precursor, (-)-(6R)-2,2,6-trimethylcyclohexan-1,4-dione, which was readily prepared by the fermentation of oxoisophorone with bakers' yeast.