473758-71-3

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 473758-71-3
• Molecular Weight: 538.846
• Mol File: 473758-71-3.mol

Chemical Properties

• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(473758-71-3)
• EPA Substance Registry System: (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(473758-71-3)

Safety Data

• Hazardous Substances Data: 473758-71-3(Hazardous Substances Data)

Upstream product

• 83021-07-2 (S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one 
• 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 
• 473758-72-4 (E)-tert-butyl(3-iodobut-2-enyloxy)diphenylsilane 
• 152187-06-9 (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene 

Downstream Products

• 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 
• 473758-70-2 3-[N⁶-biotinyl-N²-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol 
• 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 

Relevant articles and documents

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.