3292-82-8

Upstream product

• 16975-62-5 tritylglycerol 
• 1235-22-9 allyl trityl ether 
• 76-83-5 trityl chloride 
• 18325-45-6 trityl 2-hydroxyethyl ether 

Downstream Products

• 3292-83-9 1-thiazol-2-yl-2-trityloxy-ethanol 
• 211488-49-2 1-(4-Methyl-1-trityl-1H-imidazol-2-yl)-2-trityloxy-ethanol 
• 170277-82-4 (2S)-1-triphenylmethoxy-4-pentene-2-ol 
• 861889-33-0 N-{1-[(4-methylphenyl)sulfonyl]-2-(trityloxy)ethyl}-P,P-diphenylphosphinamide 
• 869967-24-8 2-[4-(2-phenylethyl)-1-(triphenylmethyl)-1H-imidazol-2-yl]-2-(triphenylmethoxy)ethanol 
• 211488-51-6 2-(1-Methoxy-2-trityloxy-ethyl)-4-methyl-1-trityl-1H-imidazole 
• 1392278-21-5 (E)-4-methyl-5-(trityloxy)pent-3-en-2-one 
• 74684-99-4 1-Trityloxy-propan-2-one 
• 71697-18-2 1,2-propyleneglycol-1-triphenylmethyl ether 

Relevant academic research and scientific papers

Total Synthesis of the Bis-silyl Ether of (+)-15-epi-Aetheramide A

Synthesis of the macrolactone depsipeptide aetheramide A was attempted by three different approaches. The first approach to form the macrolactone involving macrolactonization to form the C1-C21 bond and the second approach using a ring-closing metathesis (RCM) strategy to form the C10-C11 olefinic bond failed. The third approach starting from R-mandelic acid, involving the RCM reaction to install the C18-C19 ring junction, was successful in assembling the macrolactone.

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at Cα, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24 N-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman's chiral sulfinamide provides chiral N-sulfinylimines, which were reacted with (trimethylsilyl)ethynyllithium to afford diastereomerically pure N-sulfinyl propargylamines. Diverse functional groups present in the propargylic position resemble the side chain present at the Cα of amino acids. Whereas propargylamines with (cyclo)alkyl substituents can be prepared in a direct manner, residues with polar functional groups require suitable protective groups. The presence of particular functional groups in the side chain in some cases leads to remarkable side reactions of the alkyne moiety. Thus, electron-withdrawing substituents in the Cα-position facilitate a base induced rearrangement to α,β-unsaturated imines, while azide-substituted propargylamines form triazoles under surprisingly mild conditions. A panel of propargylamines bearing fluoro or chloro substituents, polar functional groups, or basic and acidic functional groups is accessible for the use as precursors of peptidomimetics.

Synthesis of azepino[4,5- b ]indolones by an intramolecular cyclization of unsaturated tryptamides

A facile general route for the synthesis of azepino[4,5-b]indolones is presented. The strategy involves a Bronsted acid assisted intramolecular cyclization of unsaturated tryptamides. The methodology developed has been applied to the synthesis of the ABCD

Total synthesis of bafilomycin A1

A convergent synthesis of bafilomycin A1, a potent inhibitor of V-type ATPases, is presented. The synthesis relies on the zinc triflate mediated diastereoselective addition of a complex enyne to a sensitive aldehyde as the key fragment coupling. A ruthenium-catalyzed trans-reduction of the resulting propargylic enyne efficiently installs the required C10-C13 trans,trans-diene subunit, implementing an alternative strategy to traditional palladium-catalyzed cross-coupling strategies. A highly selective oxidation of a secondary hydroxyl group in a triol sets the stage for the completion of the synthesis. Copyright

Palladium-catalyzed asymmetric quaternary stereocenter formation

An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright

Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[al] process): A simple access to γ-lactols and 4-methylene-γ-lactols

An efficient preparation of γ-lactols and methylene-γ-lactols is described. Highly acid-sensitive lactols are prepared in a concise manner by using a radical cyclization of aluminum acetals. The precursors for the radical reactions are readily prepared fr

Tishchenko reactions of aldehydes promoted by diisobutylaluminum hydride and its application to the macrocyclic lactone formation

Aliphatic aldehydes react with catalytic amount of Dibal-H in n-pentane to give the corresponding Tishchenko products in good to excellent yields. On contrary, α-silyloxy aldehydes give α-silyloxy ketones via Oppenauer oxidation under similar condition. Tishchenko reaction of ω-alkene aldehydes followed by RCM and hydrogenation affords a convenient method to prepare the 11-37 membered macrocyclic lactones.

Syntheses of α,β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides

Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-αβ-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-αβ-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed. (C) 2000 Elsevier Science Ltd.

Enantioselective allyltitanations. Synthesis of optically active 1,2- diol units: Useful intermediates for the preparation of biologically active compounds

1,2-Diol units were synthesized with excellent enantiomeric excess by using an enantioselective allyltitanation of α-alkoxy-substituted aldehydes.

Synthesis of 1-(1H-imidazol-2-yl)ethane-1,2-diol derivatives: A novel class of protein kinase C inhibitors

Compounds 6-13 were prepared starting from 1-(triphenlymethyl)-protected 1H-imidazoles 14 and 15 in several steps. Lithiation with BuLi in THF followed by reaction with (triphenylmethoxy)acetaldehyde (16) afforded 17 and 18, respectively. O-Methylation of