152187-06-9

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 130583-95-8 (4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one 
• 20548-02-1 (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one 
• 60046-49-3 (6R)-levodione 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 152187-07-0 Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate 
• 83021-07-2 (S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one 
• 439859-82-2 4-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester 
• 875797-47-0 (-)-(2E,4E)-5-[(R)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3-methylpenta-2,4-dien-1-ol 
• 875927-53-0 (-)-(R)-13-cis-3-hydroxyretinal 
• 76686-34-5 ethyl (-)-(R)-all-trans-3-hydroxyretinoate 
• 875797-48-1 (-)-(R)-all-trans-3-(tert-butyldimethylsilyloxy)retinol 
• 875927-54-1 ethyl (-)-(R)-all-trans-3-(tert-butyldimethylsilyloxy)-retinoate 
• 121468-88-0 (-)-(2E,4E)-5-[(R)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3-methylpenta-2,4-dienal 
• 60046-53-9 (-)-(R)-all-trans-3-hydroxyretinal 
• 60046-52-8 all-trans-(3R)-3-Hydroxyretinol 
• 909128-70-7 (R)-4-acetoxy-2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate 
• 909128-71-8 (1R,3'E)-4-(5-hydroxy-3-methylpent-3-en-1-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl acetate 
• 322474-86-2 1,1-dimethylethyl{[(1R)-4-ethynyl-3,5,5-trimethylcyclohex-3-entl]oxy}dimethylsilane 

Relevant academic research and scientific papers

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).

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.

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