A5069511788- Chemistry and Chemical Engineering
- Inorganic and Organometallic Chemistry
- Asymmetric Synthesis and Catalysis
- Oxidative Organic Chemistry Reactions
- Catalytic Cross-Coupling Reactions
- Crystallization and Solubility Studies
- Chemical synthesis and alkaloids
- Vanadium and Halogenation Chemistry
- Synthetic Organic Chemistry Methods
- Sulfur-Based Synthesis Techniques
- X-ray Diffraction in Crystallography
- Fluorine in Organic Chemistry
- Chemical Reactions and Isotopes
- Chemical Synthesis and Analysis
- Click Chemistry and Applications
- Catalytic C–H Functionalization Methods
- Marine Toxins and Detection Methods
- Chemical Synthesis and Reactions
- Marine Sponges and Natural Products
- Carbon dioxide utilization in catalysis
- Innovative Microfluidic and Catalytic Techniques Innovation
- Phenothiazines and Benzothiazines Synthesis and Activities
- Chromatography in Natural Products
- Steroid Chemistry and Biochemistry
- Bioactive Compounds and Antitumor Agents
Bristol-Myers Squibb (United States)
2017-2025
The Bristol-Myers Squibb Children's Hospital
2017-2022
Scripps Research Institute
2015
Columbia University
2009-2013
Cornell University
2009
Centre National de la Recherche Scientifique
2009
Université de Rennes
2009
Borealis (Finland)
2009
Chimie ParisTech
2009
Although there are many reagent combinations that can initiate polyene cyclizations, simple electrophilic halogen sources have not yet proven broadly effective as promoters of such processes. Herein is described a readily prepared and stable class reagents capable effecting transformations for wide range electron-rich -deficient terpenes derived from geraniol, farnesol, nerol, thereby enabling the synthesis diverse array complex chlorine-, bromine-, iodine-containing polycyclic frameworks....
The ring-opening polymerization of a mixture enantiomerically pure but different monomers using an yttrium complex as initiator proceeds readily at room temperature to give the corresponding highly alternating polyester.
It's all about reactivity: Although bromonium-induced cation–π cyclizations are commonly utilized by nature to fashion six-membered rings from a diverse set of polyene precursors, no general laboratory method exists that can achieve the same breadth substrate scope. An easily synthesized and handled reagent is described (see scheme) capable directly, broadly, rapidly effecting such reactions in good yield with variety geraniol, farnesol, nerol derivatives.
A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- 9-membered bromoethers in regio- stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble cores Laurencia C15 acetogenins. In light generality effectiveness approach, this work provides strategy for their laboratory preparation may implicate possible...
Herein is presented a cohesive strategy to rapidly fashion diverse members of the lauroxocane family natural products, leading shortest syntheses any member date. These efforts include racemic formal total laurefucin and E- Z-pinnatifidenyne as well facile preparation oxocene core 3E-dehydrobromolaurefucin. The key elements design are novel diastereoselective ring-expanding bromoetherifications tetrahydrofurans triggered by unique bromonium source (BDSB, Et2SBr·SbBrCl5) strategically...
Deucravacitinib (BMS-986165) is a deuterated small-molecule TYK2 inhibitor developed for the treatment of numerous autoimmune disorders. While first-generation discovery chemistry route to access deucravacitinib was concise and sufficient kilogram quantities API, impurity control cost-of-goods concerns necessitated design new route. Once identified demonstrated, each step optimized yield, purity, robustness, sustainability. Key accomplishments include (1) development novel cyclocondensation...
Reaktivität ist alles: Obwohl Bromonium-induzierte Kation-π-Cyclisierungen zum Aufbau sechsgliedriger Ringe in der Natur weit verbreitet sind und dabei auf einen vielfältigen Satz von Polyen-Vorstufen zurückgreifen, existiert kein Labormethode, die gleiche Substratbreite erreichen würde. Ein leicht zugängliches einfach zu handhabendes Reagens wird beschrieben (siehe Schema), das Geraniol-, Farnesol- Nerol-Derivate direkt, schnell hohen Ausbeuten solchen Reaktionen umsetzt. Detailed facts of...
The search for a faster, safer protocol the direct synthesis of 5-aryltetrazoles from aryl nitriles in presence sodium azide and an amine hydrochloride salt led to discovery buffered system comprised BnNH2, BnNH2·HCl, NaN3. After optimization reaction conditions thorough investigation safety, procedure was demonstrated several hundred grams 4-chloro-2-(2H-tetrazol-5-yl)phenol. generality developed established by small-scale reactivity screen using 16 additional heteroaryl nitrile substrates.
Zinc salts have been shown to promote the Buchwald-Hartwig coupling of azaindoles and azaindazoles with heteroaryl chlorides provide corresponding 1-aryl-1H-azaindoles 1-aryl-1H-azaindazoles. The substrate scope mechanistic aspects this reaction were explored.
A highly stereoselective synthesis of a cyclic dinucleotide (CDN) STING agonist containing two chiral thiophosphoramidate linkages is described. These rare yet key functional groups were, for the first time, installed efficiently and with high diastereoselectivity using specially designed P(V) reagent. By utilizing this strategy, CDN was prepared in greater than 16-fold higher yield prior P(III) approach, fewer hazardous reagents chromatographic purifications.
ADVERTISEMENT RETURN TO ISSUEPREVGreen Chemistry High...Green HighlightsNEXTGreen Articles of Interest to the Pharmaceutical IndustryMelissa A. AshleyMelissa AshleyGenentech Inc., 1 DNA Way, South San Francisco, California 94080, United StatesMore by Melissa Ashley, Miles H. AuklandMiles AuklandChemical Development, Technology & Operations, AstraZeneca, Macclesfield SK10 2NA, U.K.More Aukland, Marian C. Bryan*Marian BryanJanssen R&D, 1400 McKean Road, Spring House, Pennsylvania 19002,...
1-Hydroxybenzotriazole (HOBt) is a nucleophilic additive widely utilized in synthetic chemistry. During process optimization for an amidation reaction employing HOBt, the presence of two hydrazide impurities was ultimately traced back to hydrazine contamination HOBt. An analytical method HOBt able quantify trace levels and 1-chloro-2-nitrobenzene (another putative mutagenic impurity) developed validated. Nearly dozen batches commercial from several vendors were tested revealed occasional,...
The definition of a robust control strategy is critical to ensuring quality in the manufacture active pharmaceutical ingredients (APIs). This publication provides case study wherein Bayesian probabilistic modeling was used evaluate process risk exceeding permitted level for impurity deucravacitinib drug substance (DS). Formation and purging this were studied via Design Experiments (DoE) univariate investigation reaction crystallization parameters. models generated predict performance assess...
ADVERTISEMENT RETURN TO ISSUEPREVGreen Chemistry High...Green HighlightsNEXTGreen Articles of Interest to the Pharmaceutical IndustryMarian C. Bryan*Marian BryanJanssen R&D, 1400 McKean Road, Spring House, Pennsylvania 19002, United States*Email: [email protected]More by Marian Bryan, Charlotte DaltonCharlotte DaltonCatSci Ltd, CBTC2, Capital Business Park, Cardiff, South Glamorgan CF3 2PX, U.K.More Dalton, Alba Díaz-RodríguezAlba Díaz-RodríguezSynthetic Biochemistry, GSK, Gunnels Wood...
ADVERTISEMENT RETURN TO ISSUEPREVGreen Chemistry High...Green HighlightsNEXTGreen Articles of Interest to the Pharmaceutical IndustryMarian C. Bryan*Marian BryanJanssen R&D, 1400 McKean Road, Spring House, Pennsylvania 19002, United States*Email: [email protected]More by Marian Bryan, Charlotte DaltonCharlotte DaltonCatSci Ltd, CBTC2, Capital Business Park, Cardiff, South Glamorgan CF3 2PX, U.K.More Dalton, Alba Díaz-RodríguezAlba Díaz-RodríguezSynthetic Biochemistry, GSK, Gunnels Wood...
Abstract Review: 165 refs.
The classical preparation of 3-methyl-1-aryl-1,2,4-triazoles through an SNAr reaction pathway results in a mixture N-regioisomers. Removal the unwanted isomer reduces yield and affects processability final product. In presented case study, target triazole was prepared by route over three steps, 24% overall yield, with prohibitive Process Mass Index (PMI) 300 that made inadequate for process scale implementation. Bristol-Myers Squibb scientists discovered improved strategy allows access to...
ADVERTISEMENT RETURN TO ISSUEPREVGreen Chemistry High...Green HighlightsNEXTGreen Articles of Interest to the Pharmaceutical IndustryCharlotte DaltonCharlotte DaltonCatSci Ltd, CBTC2, Capital Business Park, Cardiff CF3 2PX, United KingdomMore by Charlotte Dalton, Louis J. DiorazioLouis DiorazioChemical Development, Technology & Operations, AstraZeneca, Macclesfield SK10 2NA, Diorazio, Jaika DoerflerJaika DoerflerAmgen, One Amgen Center Drive, Thousand Oaks, California 91320, StatesMore...