73448-14-3

Upstream product

• 53293-00-8 hex-5-ynoic acid 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 540-88-5 acetic acid tert-butyl ester 
• 32264-79-2 but-3-yn-1-yl trifluoromethanesulfonate 
• 75-65-0 tert-butyl alcohol 
• 77758-51-1 methyl hex-5-ynoate 

Downstream Products

• 945965-65-1 methyl 5-(5-tert-butoxycarbonyl-pent-1-ynyl)-2-methoxy-3-methylbenzoate 
• 845272-51-7 3-[5-(tert-butyloxycarbonyl)pent-1-ynyl]-4,4'-dimethoxybenzophenone 
• 21963-38-2 5-vinyl-dihydrofuran-2(3H)-one 
• 928-91-6 (Z)-4-hexenol 
• 945965-68-4 (E)-tert-butyl 6-(4-methoxy-3-(methoxycarbamoyl)-5-methylphenyl)-6-(tributylstannyl)hex-5-enoate 
• 945965-66-2 (E)-methyl 5-(6-tert-butoxy-6-oxo-1-(tributylstannyl)hex-1-enyl)-2-methoxy-3-methylbenzoate 
• 945965-67-3 (E)-5-(6-tert-butoxy-6-oxo-1-(tributylstannyl)hex-1-enyl)-2-methoxy-3-methylbenzoic acid 
• 1065027-90-8 (Z)-5-((1Z,6Z)-6-bromo-1-(3,7-dimethyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)-6-(methoxylmino)hex-1-enyl)-N,2-dimethoxy-3-methylbenzimidoyl bromide 
• 1065027-89-5 (Z)-5-((1E,6Z)-6-bromo-1-(3,7-dimethyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)-6-(methoxylmino)hex-1-enyl)-N,2-dimethoxy-3-methylbenzimidoyl bromide 
• 927960-73-4 4-[5-chloro-1-(4-methoxyphenyl)sulfonylindol-2-yl]butanoic acid 
• 927960-83-6 4-[5-chloro-1-(3-methoxyphenyl)sulfonylindol-2-yl]butanoic acid 

Relevant academic research and scientific papers

Total Synthesis of the Plant Growth Promoter Auxofuran Featuring a Gold(I) Catalyzed Furan Formation

A concise synthesis of auxofuran (1) was developed. Starting with a Sonogashira cross-coupling reaction, enynol (10) was prepared. A gold(I) catalyzed cycloisomerization led to disubstituted furan 12. Via an intramolecular Friedel-Crafts cyclization, a dihydrobenzofuranone was obtained. Functional group manipulations, including benzylic oxidation, led to the target molecule.

Migratory Hydrogenation of Terminal Alkynes by Base/Cobalt Relay Catalysis

Migratory functionalization of alkenes has emerged as a powerful strategy to achieve functionalization at a distal position to the original reactive site on a hydrocarbon chain. However, an analogous protocol for alkyne substrates is yet to be developed. Herein, a base and cobalt relay catalytic process for the selective synthesis of (Z)-2-alkenes and conjugated E alkenes by migratory hydrogenation of terminal alkynes is disclosed. Mechanistic studies support a relay catalytic process involving a sequential base-catalyzed isomerization of terminal alkynes and cobalt-catalyzed hydrogenation of either 2-alkynes or conjugated diene intermediates. Notably, this practical non-noble metal catalytic system enables efficient control of the chemo-, regio-, and stereoselectivity of this transformation.

Hexayne Amphiphiles and Bolaamphiphiles

Oligoynes with two or more conjugated carbon–carbon triple bonds are useful precursors for carbon-rich nanomaterials. However, their range of applications has so far been severely limited by the challenging syntheses, particularly in the case of oligoynes

A boron-based Ireland-Claisen approach to the synthesis of pordamacrine A

A synthetic approach to pordamacrine A that features two key transformations is discussed. The first transformation applies an Ireland-Claisen rearrangement to establish sterically congested vicinal carbon centers. Although a hard enolization technique for accessing the silyl ketene acetal failed, a soft enolization, boron-based reaction was highly successful. The second step involves a proposed cascade palladium-catalyzed biscyclization to construct two carbocycles of the natural product. The overall strategy is presented, demonstrating the challenges of the cyclization events in this complex setting.

Water-soluble prodrug of antimicrotubule agent plinabulin: Effective strategy with click chemistry

Click for improved solubility: A water-soluble prodrug of plinabulin was designed and synthesized efficiently by using click chemistry in three steps (see scheme). The product was highly water-soluble, and the parent compound could be regenerated by ester

ALKENYLDIARYLMETHANES HAVING NITROGEN-CONTAINING CARBOXYLIC ACID DERIVATIVES

Alkenydiarylmethane compounds are described. Such compounds are a class of non-nucleoside inhibitors of HIV-I reverse transcriptase, which may also be used as part of a combination therapy to treat HIV infection. Compounds described herein exhibit antivir

Reaction of dicarbonates with carboxylic acids catalyzed by weak Lewis acids: General method for the synthesis of anhydrides and esters

The reaction between carboxylic acids (RCOOH) and dialkyl dicarbonates [(R1OCO)2O], in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol (R1OH) as the solvent, leads to the esters RCOOR1 in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride [(RCO)2O], R1OH and carbon dioxide. The esters arise from the attack of the alcohols on the anhydrides. Exploiting the lesser reactivity of tert-butyl alcohol in comparison with other alcohols, a clean synthesis of both carboxylic anhydrides and esters has been set up. In the former reaction, an acid/Boc2O molecular ratio of 2:1 leads to the anhydride in good to excellent yields, depending on the stability of the resulting anhydride to the usual workup conditions. In the latter reaction, stoichiometric mixtures of the acid and Boc2O are allowed to react with a twofold excess of a primary alcohol, secondary alcohol or phenol (R 2OH) to give the corresponding esters (RCOOR2). Purification of the products is particularly easy since all byproducts are volatile or water soluble. A very easy chromatography is required only in the case of nonvolatile alcohols. A broad variety of sensitive functional groups is tolerated on both the acid and the alcohol, in particular a high chemoselectivity is observed. In fact, no transesterification processes occur with the acid-sensitive acetoxy group and methyl esters. Georg Thieme Verlag Stuttgart.

Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2

The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G2, creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.

Synthesis and anti-HIV activity of new metabolically stable alkenyldiarylmethane non-nucleoside reverse transcriptase inhibitors incorporating N-methoxy imidoyl halide and 1,2,4-oxadiazole systems

The alkenyldiarylmethanes (ADAMs) are a unique class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) that are capable of inhibiting HIV-1 reverse transcriptase (RT) through an allosteric mechanism. However, the potential usefulness of the ADAM

Derivatised molecules for mass spectrometry

Compounds of formula (IIa): are provided where:X is a group capable of being cleaved from the α-carbon atom to form an ion of formula (I')C is a carbon atom bearing a single positive charge or a single negative charge; The invention further provides compounds of formula (IIb): where:X is a counter-ion to C. The compounds of formula (IIa) and (IIb) may form ions of formula (I') by either cleaving the C-X bond between X and the α-carbon atoms in the case of the compounds of formula (IIa) or dissociating X in the case of compounds of formula (IIb).