180577-83-7

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 540-38-5 p-Iodophenol 
• 105633-68-9 triisopropyl((1-phenyl)oxy)silane 
• 94-18-8 Benzyl 4-hydroxybenzoate 

Downstream Products

• 643090-88-4 N-Boc-D-Phe-ΔTyr(OTIPS)-OMe 
• 643090-93-1 (4-((triisopropylsilyl)oxy)phenyl)boronic acid 
• 643090-94-2 N-Boc-D-Phe-ΔTyr(OTIPS)-CH2OH 
• 643090-87-3 N-Boc-D-Phe-V-ΔTyr(OTIPS)-OMe 
• 478910-85-9 6,7-dimethoxy-8-[4-(triisopropylsilanyloxy)phenyl]isochroman-1-one 
• 473840-66-3 2-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5,6-dimethoxy-4'-triisopropylsilanyloxy-biphenyl-3-yl]-ethanol 
• 478910-88-2 N-{2-[2-ethynyl-5,6-dimethoxy-4'-(triisopropylsilanyloxy)biphenyl-3-yl]ethyl}-4-methylbenzenesulfonamide 
• 1071910-93-4 (4-benzofuran-2-yl-phenoxy)-triisopropyl-silane 
• 1131040-29-3 2-(4-triisopropylsilanyloxyphenyl)quinoxaline 
• 1194341-09-7 ethyl 2-chloro-4-{4-[(triisopropylsilyl)oxy]phenyl}nicotinate 
• 1176869-92-3 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile 
• 1224598-06-4 2-bromo-7-(4-[(triisopropylsilyl)oxy]phenyl)quinolin-8-yl N,N,N',N'-tetramethyldiamidophosphate 
• 1311295-48-3 C₂₈H₄₂N₂O₄Si 

Relevant academic research and scientific papers

Total synthesis of ent-(+)-cinanthrenol A

The first total synthesis of ent-(+)-cinanthrenol A of potent estrogenic activity was achieved with 10.9% overall yield in 13 steps from commercially available materials. Our synthesis features a photo-promoted oxidative 6π-electron electrocyclization/aromatization for construction of the cyclopentaaphenanthren-17-one and Furukawa hydroxyl-directed cyclopropanation for the rare spiro2,4heptane. The brevity of this synthetic strategy would allow an expedited access to cinanthrenol A and its analogs for further biological evaluation.

SS-AMINO ACID DERIVATIVE, KINASE INHIBITOR AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME, AND USE OF THE SAME

A compound represented by Formula (I), a pharmaceutically acceptable salt or ester, hydrate, solvate or crystalline form thereof is provided: The compound represented by Formula (I) is a β-amino acid derivative, and in Formula (I): X is a single bond or O; Y is NH or C=O; Z is C=O, C=S, NH, W is C or N; A is a single bond, O, OH, OCH2, a heterocycle or N3; R1 is H or F; R2 is H, F, OH, CF3, CH2OH, CHO or ; R3 is H; n is 0 or 1; and m is 0 or 1.

Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles

The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles.

Synthesis of β-Arylethenesulfonyl Fluoride via Pd-Catalyzed Nondirected C-H Alkenylation

A rapid synthesis of β-arylethenesulfonyl fluorides is realized using ligand-accelerated Pd(II)-catalyzed nondirected C-H alkenylation of simple arenes. The newly developed electron-deficient 2-pyridone ligand is crucial for this transformation with arenes as limiting reagent. This protocol features a broad substrate scope and good functional group tolerance. Late-stage functionalization of various pharmaceuticals and their further click manipulations demonstrate this procedure to be highly valuable.

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

TLR-INDEPENDENT SMALL MOLECULE ADJUVANTS

A TLR-independent adjuvant compound that corresponds in structure to Formula I, below, or its pharmaceutically acceptable salt is disclosed in which X, Y, Z, n, R1, R2, R3, R4 and W are defined within. Also disclosed are a method of its preparation and use, as well as a pharmaceutical composition containing the same.

Discovery and Structure-Activity Relationships of the Neoseptins: A New Class of Toll-like Receptor-4 (TLR4) Agonists

Herein, we report studies leading to the discovery of the neoseptins and a comprehensive examination of the structure-activity relationships (SARs) of this new class of small-molecule mouse Toll-like receptor 4 (mTLR4) agonists. The compounds in this class, which emerged from screening an α-helix mimetic library, stimulate the immune response, act by a well-defined mechanism (mouse TLR4 agonist), are easy to produce and structurally manipulate, exhibit exquisite SARs, are nontoxic, and elicit improved and qualitatively different responses compared to lipopolysaccharide, even though they share the same receptor.

Gold(I)-catalyzed iodination of arenes

A wide variety of electron-rich arenes were efficiently converted into the corresponding iodinated compounds via a gold(I)-catalyzed reaction under mild conditions. Georg Thieme Verlag Stuttgart. New York.

NEOSEPTINS: SMALL MOLECULE ADJUVANTS

A MD-2:TLR4 complex agonist compound is disclosed whose structure corresponds to Formula (I), as defined within. Also disclosed are a method of its preparation and use, as well as a pharmaceutical composition containing the same.

2-Methoxy-4-nitrobenzenediazonium salt as a practical diazonium-transfer agent for primary arylamines via tautomerism of 1,3-diaryltriazenes: Deaminative iodination and arylation of arylamines without direct diazotization

1,3-Diaryltriazenes, prepared from a 2-methoxy-4-nitrobenzenediazonium salt and primary arylamines, exist as "azo-transfer" tautomers in which the 2-methoxy-4-nitrophenyl group is present on the saturated nitrogen atom and forms a hydrogen bond between the 2-methoxy group and the N-H moiety. The synthetic utility of the diazonium salt as a practical diazonium-transfer agent for primary arylamines via tautomerism of the 1,3-diaryltriazenes has been demonstrated by the deaminative iodination and arylation of the arylamines without direct diazotization. The starting 2-methoxy-4-nitrophenylamine can be easily recovered after the reactions.