3329-88-2

Usage

Functional groups

Alkyne, Tosylate (p-Tosyloxy) group

Use in organic synthesis

Reagent for the introduction of the alkyne functional group into molecules

Reactivity

Ability to undergo reaction with various nucleophiles to form new carbon-carbon bonds

Versatility

Tosylate group provides a good leaving group for substitution reactions

Applications

Construction of complex organic molecules, synthesis of pharmaceuticals and agrochemicals

Importance

Valuable tool in organic chemistry, important intermediate in the synthesis of various compounds

InChI:InChI=1/C12H14O3S/c1-3-4-5-10-15-16(13,14)12-8-6-11(2)7-9-12/h6-9H,5,10H2,1-2H3

Upstream product

• 10229-10-4 pent-3-yn-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 54106-83-1 pent-3-ynyl triflate 

Downstream Products

• 73023-94-6 3-Methyl-2-pent-3-ynyl-cyclohex-2-enone 
• 765-43-5 Cyclopropyl methyl ketone 
• 646-05-9 pent-1-en-3-yne 
• 53968-68-6 2-methylcyclobutenyl 2,2,2-trifluoroethyl ether 
• 97487-36-0 4-methylbut-3-yn-1-yl 2,2,2-trifluoroethyl ether 
• 10229-10-4 pent-3-yn-1-ol 
• 1517-15-3 2-methylcyclobutanone 
• 165461-04-1 N-Benzyl-N-(pent-3-ynyl)-N-(prop-2-ynyl)amine 
• 1285256-94-1 C₂₂H₂₂O₄ 
• 1285256-96-3 dibenzyl 2-allyl-2-(4-methyl-3-methylenepent-4-enyl)malonate 
• 145782-28-1 (E)-2-(1-phenylethylidene)-1-tosylpyrrolidine 
• 145782-20-3 N-hex-4-ynyl-(4-methylbenzene)sulfonamide 
• 283611-65-4 2-(Diethoxy-phosphoryl)-pentanedioic acid 5-tert-butyl ester 1-[(1R,2R,3S,4R)-3-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-4-((E)-oct-6-enyl)-6-oxo-cyclohexyl] ester 
• 283611-59-6 tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate 

Relevant academic research and scientific papers

Synthesis of Morpholine-Based Analogues of (?)-Zampanolide and Their Biological Activity

We describe the convergent synthesis of three prototypical examples of a new class of analogues of the complex, cytotoxic marine macrolide (?)-zampanolide that incorporate an embedded N-substituted morpholine moiety in place of the natural tetrahydropyran ring. The final construction of the macrolactone core was based on a high-yielding intramolecular HWE olefination, while the hemiaminal-linked side chain was elaborated through a stereoselective, BINAL-H-mediated addition of (Z,E)-sorbamide to a macrocyclic aldehyde precursor. The synthesis of the common functionalized morpholine building block involved two consecutive epoxide openings with tosylamide and the product of the first opening reaction, respectively, as nucleophiles. Of the three morpholino-zampanolides investigated, the N-acetyl and the N-benzoyl derivatives both exhibited nanomolar antiproliferative activity, thus being essentially equipotent with the natural product. In contrast, the activity of the N-tosyl derivative was significantly reduced.

Pyridopyril compound and medical application thereof

The invention relates to a pyridine ring compound and a medical application thereof as shown in a formula (I). The invention further relates to a preparation method of the compound. Use of a pharmaceutical composition and as FGFR4 inhibitor for the treatment of cancer.

Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis

A highly enantioselective and diastereoselective total synthesis of the diterpenoid (-)-mitrephorone A is presented. Key to the synthesis are stereocontrolled 1,4-semihydrogenation of a 1,3-diene to a tetrasubstituted double bond, enzyme-catalyzed malonat

Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst

An efficient and highly enantioselective Conia-ene-type process has been developed. Reactions are catalyzed by a combination of B(C6F5)3, an N-alkylamine and a BOX-ZnI2 complex. Specifically, through cooperative

TETRAHYDROISOQUINOLINE DERIVATIVES

Compounds of Formula (I) are disclosed and methods of treating viral infections with compositions comprising such compounds.

A copper-catalyzed pyrrolidine and preparation of quinoline derivatives method and application (by machine translation)

The invention discloses a pyrrolidine and for preparation of quinoline derivatives, comprises the following steps: the cuprous chloride and aminoalkynes, alkynes are added to a reaction flask, adding the solvent DMF, under microwave irradiation, 150 °C reaction 30 minutes to obtain the target product. The method has high yield, time fast, low cost, for the end of the substrate is not limited to the alkyne, to non-terminalthe alkyne is eventerminal alkyne and has good serviceability, solves the defect of the gold catalytic of this reaction, the method for preparing the compound portion of through the cell active test, with tumor cell proliferation inhibitory activity, indicates this method is in the anti-tumor drug discovery has potential application value. (by machine translation)

SYNTHESIS OF ENT-PROGESTERONE AND INTERMEDIATES THEREOF

The present invention relates to the synthesis of ent-progesterone and intermediates thereof.

Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of γ-, δ- and ?-Lactones

The improved synthesis of γ-, δ- and ?-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to γ- and δ-lactones in high regio- and stereoselectivity. Reactions were performed at l

HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME

Disclosed are compounds of formula (I): or a pharmaceutically acceptable salt thereof; wherein Y, Ra, Ra', Rc, Rf, X2, Rd, Rd', Re, Re', m, and G have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry, useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular and neurodegenerative diseases or disorders.

Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin

Astellatol and nitidasin belong to a subset of sesterterpenoids that share a sterically encumbered trans-hydrindane motif with an isopropyl substituent. In addition, these natural products feature intriguing polycyclic ring systems, posing significant challenges for chemical synthesis. Herein, the evolution of our stereoselective strategy for isopropyl trans-hydrindane sesterterpenoids is detailed. These endeavors included the synthesis of several building blocks, enabling studies toward all molecules of this terpenoid subclass, and of advanced intermediates of our initial route toward a biomimetic synthesis of astellatol. These findings provided the basis for a second-generation and a third-generation approach toward astellatol that eventually culminated in the enantioselective total synthesis of (-)-nitidasin. In particular, a series of substrate-controlled transformations to install the ten stereogenic centers of the target molecule was orchestrated and the carbocyclic backbone was forged in a convergent fashion. Furthermore, the progress toward the synthesis of astellatol is disclosed and insights into some observed yet unexpected diastereoselectivities by detailed quantum-mechanical calculations are provided. Two and a half molecules: Astellatol and nitidasin are polycyclic sesterterpenoids, posing considerable challenges for synthetic chemists. In this full account, the evolution of a synthetic strategy for these and structurally related natural products is given (see scheme). The presented work includes efforts toward a biomimetic synthesis of astellatol, a successful route for the first total synthesis of (-)-nitidasin, and quantum-mechanical investigations into unexpected diastereosectivities.