116700-73-3

Usage

Physical state

Colorless, flammable liquid

Odor

Faint

Use

Reagent in organic synthesis, protective agent for hydroxyl groups in organic compounds

Applications

Modification of natural products, synthesis of pharmaceuticals, agrochemicals, and functional materials

Properties

Ability to form stable silicon-oxygen bonds, useful in chemical transformations and as a protecting group in the synthesis of complex organic molecules

Importance

Versatile and valuable reagent in organic chemistry

Upstream product

• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 111160-83-9 tert-butyldimethyl(2-methylallyloxy)silane 
• 144828-45-5 2-(tert-butyl-dimethyl-silanyloxymethyl)-acrylic acid methyl ester 
• 3513-81-3 2-(Hydroxymethyl)allyl alcohol 
• 116700-77-7 ethyl 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)acrylate 

Downstream Products

• 881398-70-5 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester 
• 881398-72-7 2-(allyl-benzyl-carbamoyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester 
• 1429308-95-1 N-[2-(tert-butyldimethylsilyloxymethyl)allyl]-N-tert-butoxycarbonyl-(4-fluorophenyl)ethynylamine 
• 1429308-96-2 3-(tert-butyldimethylsilyloxymethyl)-5-(4-fluorophenyl)pyridine 
• 1263188-79-9 2-bromo-1-{3-{[tert-butyl(dimethyl)silyl]oxy}-2-[(4-iodophenoxy)methyl]propyl}-4-nitro-1H-imidazole 
• 1263188-78-8 tert-butyl {3-iodo-2-[(4-iodophenoxy)methyl]propoxy}dimethylsilane 
• 1263188-77-7 3-{[tert-butyl(dimethyl)silyl]oxy}-2-[(4-iodophenoxy)methyl]-1-propanol 

Relevant academic research and scientific papers

Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in staphylococcus aureus

Interfering with bacterial cell-to-cell communication is a promising strategy to combat antimicrobial resistance. The natural product hamamelitannin and several of its analogues have been identified as quorum sensing inhibitors. In this paper the synthesi

Synthesis and antiviral evaluation of novel exomethylene acyclic nucleosides and phosphonic acid nucleosides

This paper describes a very simple synthesis route of novel acyclic nucleosides and phosphonic acid nucleosides. The condensation of the mesylates 6 and 17 with the natural nucleosidic bases (A, C, U, T) under nucleophilic substitution (K2CO3, 18-Crown-6, DMF) and deprotection afforded the target nucleosides (11, 12, 13, 14) and phosphonic acid nucleosides (22, 23, 24, 25). In addition, these compounds were evaluated for their antiviral properties against various viruses. Uracil derivative 24 shows significant anti-HCMV activity (EC50 = 10.24 μM).

Synthesis of novel 6,11-o-bridged bicyclic ketolides via a palladium-catalyzed bis-allylation

(Chemical equation presented) A bridging chemistry process was developed to form an ether bridge between 6-O and 11-O of erythromycin A via a tandem or stepwise palladium-catalyzed bis-π-allylation. By applying this bridging process, new 6,11-O-bridged bicyclic ketolides (BBKs) were synthesized. These BBKs showed good antibacterial activities against the macrolide-susceptible strains as well as mef-resistant strains and served as a good core for further modifications to study the structure-activity relationship (SAR) and to overcome bacterial resistance.

A practical total synthesis of gelastatins

The first and practical total synthesis of gelastatins 1, a novel matrix metalloproteinase inhibitor possessing antitumor activity, was accomplished in nine steps starting from Meldrum's acid.

All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration

1,3-Enynes containing allylic hydrogens cis to the alkyne function as three-carbon components in rhodium(III)-catalyzed, all-carbon [3+3] oxidative annulations to produce spirodialins. The proposed mechanism of these reactions involves the alkenyl-to-ally

Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.

Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter

A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.

Small Molecule Inhibitors of KRAS G12C Mutant

The disclosure provides compounds of Formula (I) or a pharmaceutically acceptable salt thereof, wherein W1, W2, Y, Z, M, L, Cy, Cz, R1, R2, R3, R4, R2a, Rs

NEW SUBSTITUTED AZAINDOLINE DERIVATIVES AS NIK INHIBITORS

The present invention relates to pharmaceutical agents useful for therapy and/or prophylaxis in a mammal, and in particular to inhibitors of NF-κB-inducing kinase (NIK - also known as MAP3K14) useful for treating diseases such as cancer, inflammatory disorders, metabolic disorders and autoimmune disorders. The invention is also directed to pharmaceutical compositions comprising such compounds, and to the use of such compounds or pharmaceutical compositions for the prevention or treatment of diseases such as cancer, inflammatory disorders, metabolic disorders including obesity and diabetes, and autoimmune disorders.

Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation

N-(α-Hydroxyacyl)-glycinesters can be used as excellent nucleophiles in Pd-catalyzed allylic alkylation. The method allows for the stereoselective introduction of a wide range of side chains, including highly functionalized ones. Both diastereomers can be accessed through variation of the reaction conditions. Furthermore, the use of stannylated carbonates introduces vinylstannane motifs, which are eligible for subsequent C-C coupling reactions.