473758-72-4

Upstream product

• 855233-47-5 3-iodo-2-buten-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 37428-58-3 (E)-β-iodocrotyl alcohol 

Downstream Products

• 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 
• 849104-13-8 C₃₆H₅₂OSi₂ 
• 286372-20-1 8-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-6-trimethylsilanyloxy-oct-2-en-4-ol 
• 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 
• 473758-69-9 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 
• 1245925-59-0 C₄₄H₇₄O₄Si₃ 

Relevant academic research and scientific papers

Total synthesis of brevisamide

A convergent synthesis of brevisamlde (1) is described based on the application of the crotyl silane-based [4 + 2]-annulatlon used for the preparation of the advanced oxygenated tetrahydropyran Intermediate 2. The side chain bearing a conjugated (E,E)-die

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.