A5025039397- Oxidative Organic Chemistry Reactions
- Synthetic Organic Chemistry Methods
- Chemical Synthesis and Analysis
- Marine Sponges and Natural Products
- Carbohydrate Chemistry and Synthesis
- Asymmetric Synthesis and Catalysis
- Chemical synthesis and alkaloids
- Chemical Synthesis and Reactions
- HIV/AIDS drug development and treatment
- Analytical Chemistry and Chromatography
- Traditional and Medicinal Uses of Annonaceae
- Advanced Synthetic Organic Chemistry
- DNA and Nucleic Acid Chemistry
- Phenothiazines and Benzothiazines Synthesis and Activities
- Click Chemistry and Applications
- Alkaloids: synthesis and pharmacology
- Synthesis and Catalytic Reactions
- Bioactive Natural Diterpenoids Research
- Pharmacogenetics and Drug Metabolism
- Cyclopropane Reaction Mechanisms
- Fibroblast Growth Factor Research
- Synthesis of heterocyclic compounds
- Quinazolinone synthesis and applications
- Angiogenesis and VEGF in Cancer
- Protein Degradation and Inhibitors
Bristol-Myers Squibb (United States)
2000-2022
Bristol-Myers Squibb (Germany)
2008-2015
The Bristol-Myers Squibb Children's Hospital
2014
Hainan Normal University
2014
Nanyang Technological University
2014
Stanford University
1995-1996
Brandeis University
1991-1994
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBiomimetic synthesis of (.+-.)-crambines A, B, C1, and C2. Revision the structure crambines B C1Barry B. Snider Zhongping ShiCite this: J. Org. Chem. 1993, 58, 15, 3828–3839Publication Date (Print):July 1, 1993Publication History Published online1 May 2002Published inissue 1 July 1993https://pubs.acs.org/doi/10.1021/jo00067a014https://doi.org/10.1021/jo00067a014research-articleACS PublicationsRequest reuse permissionsArticle...
A series of amino acid ester prodrugs the dual VEGFR-2/FGFR-1 kinase inhibitor 1 (BMS-540215) was prepared in an effort to improve aqueous solubility and oral bioavailability parent compound. These were evaluated for their ability liberate drug vitro vivo systems. The l-alanine prodrug 8 (also known as brivanib alaninate/BMS-582664) selected a development candidate is presently phase II clinical trials.
Described herein is the synthesis of BMS-986001 by employing two novel organocatalytic transformations: 1) a highly selective pyranose to furanose ring tautomerization access an advanced intermediate, and 2) unprecedented small-molecule-mediated dynamic kinetic resolution variety enantiopure pyranones, one which served as versatile building block for multigram, stereoselective, chromatography-free BMS-986001. The required five chemical transformations resulted in 44% overall yield.
A strategy to prepare compounds with multiple chirality axes, which has led a concise total synthesis of compound 1A complete stereocontrol, is reported.
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTFrom Furan to NucleosidesBarry M. Trost and Zhongping ShiView Author Information Department of Chemistry, Stanford University Stanford, California 94305-5080 Cite this: J. Am. Chem. Soc. 1996, 118, 12, 3037–3038Publication Date (Web):March 27, 1996Publication History Received6 November 1995Published online27 March 1996Published inissue 1 January...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal synthesis of (.+-.)-chondrillin, (.+-.)-plakorin, and related peroxy ketals. Development a general route to 3,6-dihydro-1,2-dioxin-3-olsBarry B. Snider Zhongping ShiCite this: J. Am. Chem. Soc. 1992, 114, 5, 1790–1800Publication Date (Print):February 1, 1992Publication History Published online1 May 2002Published inissue 1 February 1992https://pubs.acs.org/doi/10.1021/ja00031a038https://doi.org/10.1021/ja00031a038research-articleACS...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA Concise Convergent Strategy to Acetogenins. (+)-Solamin and AnalogsBarry M. Trost Zhongping ShiCite this: J. Am. Chem. Soc. 1994, 116, 16, 7459–7460Publication Date (Print):August 1, 1994Publication History Published online1 May 2002Published inissue 1 August 1994https://pubs.acs.org/doi/10.1021/ja00095a080https://doi.org/10.1021/ja00095a080research-articleACS PublicationsRequest reuse permissionsArticle Views915Altmetric-Citations61LEARN ABOUT...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBiomimetic synthesis of the pentacyclic nucleus ptilomycalin ABarry B. Snider and Zhongping ShiCite this: J. Am. Chem. Soc. 1994, 116, 2, 549–557Publication Date (Print):January 1, 1994Publication History Published online1 May 2002Published inissue 1 January 1994https://pubs.acs.org/doi/10.1021/ja00081a015https://doi.org/10.1021/ja00081a015research-articleACS PublicationsRequest reuse permissionsArticle Views531Altmetric-Citations54LEARN ABOUT...
The evolution of a process for the preparation new heterocyclic dual NK1/serotonin receptor antagonist is described. final synthesis features telescoped sequence in which an iron(III)-catalyzed Grignard coupling followed by benzylic chlorination utilizing trichlorocyanuric acid to construct unsymmetrical 2,4,6-trisubstituted pyridine. Etherification 4,4′-arylhydroxymethane substituted piperidine fragment completes active pharmaceutical ingredient 44% overall yield.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBiomimetic synthesis of the bicyclic guanidine moieties crambines A and BBarry B. Snider Zhongping ShiCite this: J. Org. Chem. 1992, 57, 9, 2526–2528Publication Date (Print):April 1, 1992Publication History Published online1 May 2002Published inissue 1 April 1992https://pubs.acs.org/doi/10.1021/jo00035a005https://doi.org/10.1021/jo00035a005research-articleACS PublicationsRequest reuse permissionsArticle Views352Altmetric-Citations34LEARN ABOUT...
The development of a practical synthesis for p38 kinase inhibitor is described. key advances include an improved route to the intermediate, substituted pyrrole, and subsequent animation utilizing O-(4-nitrobenzoyl)hydroxylamine, which provides safe, scalable, robust amination method. new protocol was successfully demonstrated generate 1.6 kg API in seven steps 26% overall yield.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of antitumor cyclic peroxy ketals related to Chondrillin and Xestins A BBarry B. Snider Zhongping ShiCite this: J. Org. Chem. 1990, 55, 22, 5669–5671Publication Date (Print):October 1, 1990Publication History Published online1 May 2002Published inissue 1 October 1990https://pubs.acs.org/doi/10.1021/jo00309a003https://doi.org/10.1021/jo00309a003research-articleACS PublicationsRequest reuse permissionsArticle...
The N-amination of heterocyclic compounds 1a−k with O-benzoylhydroxylamine derivatives 5 was developed and demonstrated to be a superior alternative existing methods. A structure−reactivity relationship study performed on variously substituted derivatives, leading the discovery novel more efficient aminating reagents 5h 5i.
Abstract Described herein is the synthesis of BMS‐986001 by employing two novel organocatalytic transformations: 1) a highly selective pyranose to furanose ring tautomerization access an advanced intermediate, and 2) unprecedented small‐molecule‐mediated dynamic kinetic resolution variety enantiopure pyranones, one which served as versatile building block for multigram, stereoselective, chromatography‐free BMS‐986001. The required five chemical transformations resulted in 44 % overall yield.
Four synthetic strategies were evaluated towards the preparation of (-)-(3R,4R)-1-benzyl-4-(benzylamino)piperidin-3-ol (1), which was constructed with control over relative and absolute stereochemistry 4,3-amino alcohol moiety. The first strategy employed a novel Rh(I) catalyzed asymmetric hydrogenation, while two other exploited existing in 2-deoxy-D-ribose, fourth explored both biocatalytic classical resolution techniques as means to impart enantioenrichment racemic intermediates en route...
By combining ceramic membrane cross-flow filtration process with photocatalytic reaction, a reactor was designed. The simulated, and it confirmed that continuous stirred tank reactor. Experiment results indicated that, using mean pore size of 0·1 µm, slurry TiO2 particles 0·27 µm could be perfectly separated recycled in the system, stable removal rate methylene blue more than 95% loading 0·5 g L−1, reaction temperature 45°C, pressure kg cm−2 velocity 3·3 m s−1.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStereochemical Dependence of Base-Catalyzed Cleavage Cyclic Peroxy KetalsBarry B. Snider, Zhongping Shi, Steven V. O'Neil, Kevin D. Kreutter, and Tracy L. ArakakiCite this: J. Org. Chem. 1994, 59, 7, 1726–1729Publication Date (Print):April 1, 1994Publication History Published online1 May 2002Published inissue 1 April 1994https://pubs.acs.org/doi/10.1021/jo00086a022https://doi.org/10.1021/jo00086a022research-articleACS PublicationsRequest reuse...
The development of a new and practical synthesis for farnesyltransferase inhibitor 1 is described. route started from 2-nitro-5-cyanotoluene (9) afforded desired in eight chemical transformations. key step involved formation sulfonamide 13 hindered β-hydroxyamine 12 through an situ protection the hydroxyl group by forming TMS ether. Ultimately, this was successfully demonstrated to generate >10 kg API 29% overall yield.
A diamine compound (3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propan-1-amine) was demonstrated to impact downstream steps in a pharmaceutical synthetic process, and control of this less than 0.015 wt % (or 150 ppm) necessary. novel, simple, sensitive liquid chromatography/mass spectrometry (LC/MS) method without the derivatization developed for in-process (IPC) be suitable use when experiments were run at small lab scale. During development LC-MS method, found significantly adsorb surface...
Censavudine is a nucleoside reverse transcriptase inhibitor (NRTI) explored clinically by Bristol Myers Squibb for the treatment of human immunodeficiency virus-1 (HIV-1). As part development process, carbon-14 labeled analog was synthesized use in absorption, distribution, metabolism, and excretion (ADME) study. A stable isotope also as mass spectrum internal standard bioanalytical assays to accurately quantify concentration drug biological samples. Carbon-14 10 steps 9% overall yield from...
Reported is the amine-catalyzed synthesis of tetrasubstituted N-hydroxypyrroles by reaction α-carbonyloximes with α,β-unsaturated aldehydes through an iminium activation strategy. A mechanism involves unusual N-selective nucleophilic Michael addition (K. Narasaka and co-workers Eur. J. Org. Chem 2005, 4505) followed intramolecular enamine aldol condensation final aromatization. The use diisopropylamine as catalyst affords under mild conditions in moderate to good yields several types R¹...