83021-07-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 50281-38-4 (3R)-3-hydroxy-β-ionone 
• 78-94-4 methyl vinyl ketone 
• 152187-06-9 (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene 
• 444122-13-8 tert-butyldimethylsilyl (R)-4-iodo-3,5,5-trimethylcyclohex-3-en-1-yl ether 
• 444122-12-7 [(4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-cyclohex-(Z)-ylidene]-hydrazine 
• 130583-95-8 (4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one 
• 60046-49-3 (6R)-levodione 
• 20548-02-1 (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one 

Downstream Products

• 50281-38-4 (3R)-3-hydroxy-β-ionone 
• 444122-14-9 (S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether 
• 83021-09-4 (-)-3-<(R)-4-(t-Butyl)dimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propen-1-ol 
• 83021-10-7 (-)-<(R)-4-t-Butyldimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propenal 
• 83021-15-2 (R)-3-(t-Butyl)dimethylsilyloxy-19,20-dinor-vitamin-A-aldehyd 
• 83021-13-0 (R)-3-(t-Butyl)dimethylsilyloxy-9,20-dinor-vitamin-A 
• 83021-11-8 (R)-3-(t-Butyl)dimethylsilyloxy-19,20-dinor-vitamin-A-saeureaethylester 
• 83021-17-4 (3R,3'R)-3,3'-Bis<(t-butyl)dimethylsilyloxy>-19,20,19'20-'tetranor-zeaxanthin 
• 144-68-3 zeaxanthin 
• 472-70-8 (3R)-cryptoxanthin 
• 214335-84-9 (R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1,3,3-trimethyl-cyclohexene 
• 76686-24-3 (1R)-3,5,5-trimethyl-4-acetoxymethylcyclohex-3-enyl acetate 
• 214335-71-4 (-)-[(S)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-enyl]methanol 
• 171771-01-0 tert-Butyl-dimethyl-((R)-3,4,5,5-tetramethyl-cyclohex-3-enyloxy)-silane 

Relevant academic research and scientific papers

Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids

The construction of the carotenoid skeleton by Pd-catalyzed Csp2?Csp2 cross-coupling reactions of symmetrical and non-symmetrical 1,10-bissilyldeca-1,3,5,7,9-pentaenes and the corresponding complementary alkenyl iodides has been developed. Reaction conditions for these bidirectional and orthogonal Hiyama–Denmark cross-coupling reactions of bisfunctionalized pentaenes are mild and the carotenoid products preserve the stereochemical information of the corresponding oligoene partners. The carotenoids synthesized in this manner include β,β-carotene and (3R,3′R)-zeaxanthin (symmetrical) as well as 9-cis-β,β-carotene, 7,8-dihydro-β,β-carotene and β-cryptoxanthin (non-symmetrical).

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.

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.

Carotenoids and related polyenes. Part 5. Lewis acid-promoted stereoselective rearrangement of 5,6-epoxy carotenoid model compounds

The novel acyclic tetrasubstituted olefinic end group and the cyclopentyl end group of carotenoids were obtained by Lewis acid-promoted stereoselective rearrangement of the epoxide end group of 5,6-epoxy carotenoids. The scope and limitation of this rearr