68690-47-1

Upstream product

• 50848-64-1 2E,6E,10E-geranylgeranyl bromide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 71816-56-3 (2E,6E,10E)-3,7,11,15-tetramethyl-9-p-tolylsulphonylhexadeca-2,6,10,14-tetraen-1-ol 
• 68799-82-6 1-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene 
• 24034-73-9 Geranylgeraniol 
• 68690-51-7 all-trans-1-benzyloxy-3,7,11,15-tetramethyl-9-p-tolylsulfonyl-2,6,10,14-hexadecatetraene 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 37905-04-7 (2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate 
• 37905-03-6 8-hydroxygeranyl acetate 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 53254-60-7 3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene 
• 73127-51-2 (2E,6E,10E)-3,7,11,15-tetramethyl-9-[(4-methylphenyl)sulfonyl]hexadeca-2,6,10,14-tetraen-1-yl acetate 
• 106-28-5 Farnesol 
• 24163-93-7 farnesyl bromide 

Downstream Products

• 78284-77-2 (2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-9-p-tolylsulphonyltetracosa-2,6,10,14,18,22-hexaen-1-ol 
• 73127-53-4 (2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-9-p-tolylsulphonyltetracosa-2,6,10,14,18,22-hexaenyl acetate 
• 68690-53-9 all-trans-1-benzyloxy-3,7,11,15,19,23-hexamethyl-9-(p-tolylsulfonyl)-2,6,10,14,18,22-tetracosahexaene 
• 257885-57-7 [(5E,9E,13E,17E,21E)-6,10,14,18,22,26-Hexamethyl-12-(toluene-4-sulfonyl)-heptacosa-5,9,13,17,21,25-hexaen-1-ynyl]-trimethyl-silane 
• 2394-68-5 ubiquinone 8 
• 22488-05-7 geranylfarnesol 
• 303-95-7 Ubichinon-7 
• 68690-48-2 (E,E,E,E)-3,7,11,15,19-pentamethyl-1-(p-toluenesulfonyl)eicosa-2,6,10,14,18-pentaene 
• 257885-59-9 (2E,6E,10E,14E)-3,7,11,15,19-Pentamethyl-5-(toluene-4-sulfonyl)-icosa-2,6,10,14,18-pentaen-1-ol 
• 257885-60-2 [(5E,9E,13E,17E,21E,25E)-6,10,14,18,22,26,30-Heptamethyl-12-(toluene-4-sulfonyl)-hentriaconta-5,9,13,17,21,25,29-heptaen-1-ynyl]-trimethyl-silane 
• 68690-49-3 1-((2E,6E,10E,14Z,18E)-3,7,11,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-1-sulfonyl)-4-methyl-benzene 
• 5905-42-0 all-trans-3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-triacontaoctaen-1-ol 
• 68690-55-1 1-((2E,6E,10E,14Z,18E,22E,26E)-1-Benzyloxy-3,7,11,15,19,23,27,31-octamethyl-dotriaconta-2,6,10,14,18,22,26,30-octaene-9-sulfonyl)-4-methyl-benzene 
• 5915-64-0 all-trans-3,7,11,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaen-1-ol 

Relevant academic research and scientific papers

A convergent stereocontrolled synthesis of [3-14C]solanesol

In this communication, we report the synthesis of 5 mCi of [3- 14C]solanesol (1) prepared from ethyl [3-14C]acetoacetate and (all-E)-octaprenyl bromide (2) in four steps, with a specific radioactivity of 19.83 mCi/mmol and with a chemical/ stereochemical and radiochemical purity of ≥ 95%. (Figure 1). Position 3 of the chain was selected for 14C labelling because of the metabolic stability of this position. Unlabelled (all-E)-octaprenyl (18) (Scheme 4) necessary for this work was prepared via a convergent iterative 'allyl-allyl' coupling approach of precursors easily derived from readily available inexpensive starting materials. Copyright

An improved convergent strategy for the synthesis of oligoprenols

A practical and highly regio- and stereoselective synthesis of oligoprenols starting from commercially available geraniol is described. The convergent synthetic strategy features the iterative allyl-allyl coupling of monomers easily derived from geraniol that contain one reacting terminal functional group and the repetitive reductive elimination of the p-toluenesulfonyl (Ts) groups.

A convergent approach to coenzyme Q

Syntheses of coenzyme Q3-8 are described, as well as related systems such as plastoquinone-5. Preparation of the higher homologues of the ubiquinones relies on two new conjunctive reagents, or "linchpins", each of which ultimately corresponds to two or three prenyl units. These allow for attachment of a polyprenyl halide at one end, followed by a Ni(0)-catalyzed cross-coupling at the other terminus with a chloromethylated p-quinone.

Stereoselective Synthesis of Solanesol and all-trans-Decaprenol

Allylic p-tolyl sulphonates (5), (14), and (16) couple with allylic bromide (7) and geranyl bromide to produce regio- and stereo-chemically pure 1,5-diene systems.The coupling of all-trans-ω-bromogeranyl acetate (7) with geranyl p-tolyl sulphone (5) and higher isoprenologues (21), (24), and (27), followed by reductive elimination of p-tolylsulphonyl group, furnishes a stereoselective synthesis of all-trans-polyprenols (3), (23), (26), and decaprenol (1b).Solanesol (1a) was synthesised using trans-4-chloroprenyl acetate (29) instead of (7).