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Usage

Uses

Used in Organic Synthesis:
1-Bromo-4-(t-butyldimethylsilyloxy)butane is used as a reagent for introducing a t-butyldimethylsilyloxy group into organic molecules, which is essential for protecting reactive functional groups during chemical reactions. This allows chemists to carry out selective reactions without affecting the protected groups, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-Bromo-4-(t-butyldimethylsilyloxy)butane is utilized as a key intermediate in the synthesis of various drugs. Its ability to protect functional groups during chemical reactions enables the production of pharmaceuticals with specific desired properties, contributing to the development of novel therapeutic agents.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, 1-Bromo-4-(t-butyldimethylsilyloxy)butane is employed in the synthesis of agrochemicals, such as pesticides and herbicides. Its protective role in chemical reactions allows for the creation of effective and targeted agrochemicals with minimal environmental impact.
Used in the Synthesis of Complex Organic Molecules:
1-Bromo-4-(t-butyldimethylsilyloxy)butane is also used in the synthesis of complex organic molecules, where its protective properties are invaluable. By shielding reactive functional groups during chemical reactions, it enables the formation of intricate molecular structures with specific applications in various fields, such as materials science and nanotechnology.

Upstream product

• 87184-99-4 4-tert-butyldimethylsilyloxybutan-1-ol 
• 33036-62-3 4-Bromo-1-butanol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 98602-83-6 4-((tert-butyldimethylsilyl)oxy)butyl methanesulfonate 

Downstream Products

• 481658-42-8 2-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-cyclohex-2-enone 
• 1058146-44-3 3-N-benzoyl-3',5'-di-O-benzoyl-2'-fluoro-2'-deoxy-5-(4-tert-butyldimethylsilyloxybutyl)-1-β-D-arabinofuranosyluracil 
• 1058146-41-0 3-N-benzoyl-3',5'-di-O-benzoyl-5-(4-tert-butyldimethylsilyloxybutyl)-2'-deoxyuridine 
• 1612781-09-5 C₃₀H₅₂O₅Si₂ 
• 1612781-03-9 C₂₇H₄₄O₅Si 
• 1612780-85-4 C₂₃H₄₀O₃Si 
• 1612780-83-2 C₂₃H₃₇F₃O₆SSi 
• 1612780-81-0 C₂₂H₃₈O₄Si 
• 1563175-23-4 1-(4-((t-butyldimethylsilyl)oxy)butyl)-4-(3′-methoxy-[1,1′-biphenyl]-4-yl)piperazine 

Relevant academic research and scientific papers

Acid-Catalyzed Intramolecular Ring-Opening Reactions of Cyclopropanated Oxabenzonorbornadienes with Carboxylic Acid Nucleophiles

The present work demonstrates the ability of carboxylic acid tethered cyclopropanated oxabenzonorbornadienes (CPOBDs) to undergo ring-opening reactions in mild acidic conditions. The optimized reaction conditions involve the use of pTsOH in DCE at 90 °C. Two regioisomers are formed but the reactions are highly regioselective towards type 3 ring-opened products. It was observed that substitution at the C5 and aryl positions of CPOBD significantly hinders the ring-opening reactions leading to decreased yields of ring-opened products, although high regioselectivity for the Type 3 ring-opened products is still maintained. Herein, the first examples of acid-catalyzed intramolecular ring-opening reactions of CPOBD with carboxylic acid nucleophiles are reported.

Synthesis of 2-Azabicyclo[m.n.0]–Alkanes and Their Application towards the Synthesis of Strychnos and Stemona Classes of Alkaloids

2-Azabicyclo[m.n.0]alkane ring systems, the conceptual precursors towards the synthesis of Strychnos and Stemona classes of alkaloids, were synthesized from tert-butyl 2-(phenylsulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylate by alkyl Grignard reaction and intramolecular cyclisation of the in situ generated ring opening product 2. The synthesized cis-hexahydroindole 3 and cis-octahydro-benzo[b]azepine 5 scaffolds were utilized to construct the advanced intermediates 25 and 35, respectively, towards the synthesis of the corresponding Strychnos and Stemona classes of alkaloids.

Extensive structure modification on luteolin-cinnamic acid conjugates leading to BACE1 inhibitors with optimal pharmacological properties

BACE1 inhibitory conjugates derived from two natural products, luteolin (1) and p-hydroxy-cinnamic acid (2), were subjected to systematic structure modifications, including various positions in luteolin segment for conjugation, different linkers (length, bond variation), as well as various substitutions in cinnamic acid segment (various substituents on benzene, and replacement of benzene by heteroaromatics and cycloalkane). Optimal conjugates such as 7c and 7k were chosen on the basis of a series of bioassay data for further investigation.

Synthesis and antitumor activity of novel pyridinium fullerene derivatives

Purpose: We have previously reported that some cationic fullerene derivatives exhibited anticancer activity, and they are expected to be a potential lead compound for an anti-drug resistant cancer agent. However, they are bis-adducts and a mixture of multiple regioisomers, which cannot be readily separated due to the variability of substituent positions on the fullerene cage. To overcome this issue, we evaluated the antiproliferative activities of a set of mono-adduct derivatives and examined their structure-activity relationship. In addition, the in vivo antitumor activity of selected derivatives was also examined. Methods: Nineteen pyridinium fullerene derivatives were newly designed and synthesized in this study. Their antiproliferative activities were evaluated using several cancer cell lines including drug-resistant cells. Furthermore, in vivo antitumor activity of several derivatives was investigated in mouse xenograft model of human lung cancer. Results: The derivatives inhibited the proliferation of cancer cell lines, including cisplatin-resistant cells and doxorubicin-resistant cells. It was also shown that compound 10 (10 μM), 13 (10 μM) and cis-14 (10 μM) induced the intracellular oxidative stress. In addition, compound 13 (20 mg/kg) and cis-14 (15 mg/kg) significantly exhibited antitumor activity in mouse xenograft model of human lung cancer. Conclusion: We synthesized a novel set of mono-adduct fullerene derivatives functionalized with pyridinium groups and found that most of them show potent antiproliferative activities against cancer cell lines and some of them show significant antitumor activities in vivo. We propose that these fullerene derivatives serve as the lead compounds for a novel type of antitumor agents.

Total Synthesis of Emmyguyacins A and B, Potential Fusion Inhibitors of Influenza Virus

Fungal glycolipids emmyguyacins A and B inhibit the pH-dependent conformational change of hemaglutinin A during replication of the Influenza virus. Herein, we report the first total synthesis and structure confirmation of emmyguyacins A and B. Our efficient route, which involves regioselective functionalization of trehalose, allows rapid access to adequate amounts of chemically pure emmyguyacin analogues including the desoxylate derivatives for SAR studies.

NO-Responsive vesicles as a drug delivery system

A rationally designed amphiphile containing a hydrophobic Hantzsch ester and a hydrophilic phosphate ester was able to form vesicles in aqueous solution, and resulted in the first example of a NO-responsive drug delivery system.

Racemic total synthesis of dactyloidin and demethyldactyloidin through the dl-proline-catalyzed Knoevenagel condensation/[4 + 2] cycloaddition cascade

An efficient approach towards the first racemic total synthesis of dactyloidin (2) and demethyldactyloidin (3) is described. Their oxygen-bridged tricyclic ketal systems were rapidly constructed by using a remarkable biomimetic Knoevenagel condensation/[4 + 2] cycloaddition cascade as the critical strategy and the 1,5-dicarbonyl segment was assembled by Grignard addition.

Steroids modified at C15. Synthesis and spectra-structure correlations

A synthesis of 15-benzoyloxybutyl-20-hydroxymethylpregn-16-enes, the intermediates in the synthesis of brassino-and ecdysteroids modified in the D ring was performed starting with 2α,3α-isopropylidenedioxy-6,6- ethylenedyoxy-5α-androst-15-ene-17-one and its 2β,3β-isomer through a sequence of reactions involving Michael addition, Wittig reaction and ene reaction. Structures of the compounds were proved by the methods of two-dimensional NMR spectroscopy. Pleiades Publishing, Ltd., 2011.

Cyclopropenium-activated cyclodehydration of diols

The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4-and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.

2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections

Acetylenic fatty acids are known to display several biological activities, but their antimalarial activity has remained unexplored. In this study, we synthesized the 2-, 5-, 6-, and 9-hexadecynoic acids (HDAs) and evaluated their in vitro activity against erythrocytic (blood) stages of Plasmodium falciparum and liver stages of Plasmodium yoelii infections. Since the type II fatty acid biosynthesis pathway (PfFAS-II) has recently been shown to be indispensable for liver stage malaria parasites, the inhibitory potential of the HDAs against multiple P. falciparum FAS-II (PfFAS-II) elongation enzymes was also evaluated. The highest antiplasmodial activity against blood stages of P. falciparum was displayed by 5-HDA (IC50 value 6.6 μg/ml), whereas the 2-HDA was the only acid arresting the growth of liver stage P. yoelii infection, in both flow cytometric assay (IC50 value 2-HDA 15.3 μg/ml, control drug atovaquone 2.5 ng/ml) and immunofluorescence analysis (IC50 2-HDA 4.88 μg/ml, control drug atovaquone 0.37 ng/ml). 2-HDA showed the best inhibitory activity against the PfFAS-II enzymes PfFabI and PfFabZ with IC 50 values of 0.38 and 0.58 μg/ml (IC50 control drugs 14 and 30 ng/ml), respectively. Enzyme kinetics and molecular modeling studies revealed valuable insights into the binding mechanism of 2-HDA on the target enzymes. All HDAs showed in vitro activity against Trypanosoma brucei rhodesiense (IC50 values 3.7-31.7 μg/ml), Trypanosoma cruzi (only 2-HDA, IC50 20.2 μg/ml), and Leishmania donovani (IC50 values 4.1-13.4 μg/ml) with generally low or no significant toxicity on mammalian cells. This is the first study to indicate therapeutic potential of HDAs against various parasitic protozoa. It also points out that the malarial liver stage growth inhibitory effect of the 2-HDA may be promoted via PfFAS-II enzymes. The lack of cytotoxicity, lipophilic nature, and calculated pharmacokinetic properties suggests that 2-HDA could be a useful compound to study the interaction of fatty acids with these key P. falciparum enzymes.