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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 9
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Original Articles

Chlorosulfates as Reagents in the Synthesis of Carboxylic Acid Esters Under Phase-Transfer Conditions

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Pages 857-864 | Published online: 19 Dec 2006

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Paula Gomes, Maria Isabel Santos, Maria Joaquina Trigo, Raquel Castanheiro & Rui Moreira. (2003) Improved Synthesis of Amino Acid and Dipeptide Chloromethyl Esters Using Bromochloromethane. Synthetic Communications 33:10, pages 1683-1693.
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BhanudasP. Kavitake, ManikraoM. Salunkhe & PrakashP. Wadgaonkar. (1997) Efficient Method for Synthesis of Methylene Diesters Using Polyethylene Glycol as a Phase Transfer Catalyst. Synthetic Communications 27:10, pages 1703-1710.
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Naoyuki Harada, Mitsuya Hongu, Takashi Tanaka, Takayuki Kawaguchi, Tomiki Hashiyama & Kenji Tsujihara. (1994) A Simple Preparation of Chloromethyl Esters of the Blocked Amino Acids. Synthetic Communications 24:6, pages 767-772.
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Articles from other publishers (30)

Charlotte Courtens, Frits van Charante, Thibaut Quennesson, Martijn Risseeuw, Paul Cos, Guy Caljon, Tom Coenye & Serge Van Calenbergh. (2023) Acyloxymethyl and alkoxycarbonyloxymethyl prodrugs of a fosmidomycin surrogate as antimalarial and antibacterial agents. European Journal of Medicinal Chemistry 245, pages 114924.
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A. P. Sarkate, P. P. Sarode, S. V. Bhandari, K. S. Karnik, I. S. Narula, B. D. Kale, V. S. Jambhorkar & A. P. Rajhans. (2022) Convenient Microwave-Assisted Chlorosulfonic Acid-Catalyzed Synthesis of Some Quinazolinones from 2-Phenylindole. Russian Journal of Organic Chemistry 58:3, pages 428-432.
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Markéta Pimková Polidarová, Petra Břehová, Martin Maxmilian Kaiser, Miroslav Smola, Martin Dračínský, Joshua Smith, Aleš Marek, Milan Dejmek, Michal Šála, Ondrej Gutten, Lubomír Rulíšek, Barbora Novotná, Andrea Brázdová, Zlatko Janeba, Radim Nencka, Evzen Boura, Ondřej Páv & Gabriel Birkuš. (2021) Synthesis and Biological Evaluation of Phosphoester and Phosphorothioate Prodrugs of STING Agonist 3′,3′-c-Di(2′F,2′dAMP). Journal of Medicinal Chemistry 64:11, pages 7596-7616.
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Saúl Silva & Christopher D. Maycock. (2018) Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate. Tetrahedron Letters 59:13, pages 1233-1238.
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D. Gómora-HerreraI.V. LijanovaO. Olivares-XometlA. ToscanoN.V. Likhanova. (2017) Synthesis of the symmetrical methylene diesters from carboxylic ionic liquids. Canadian Journal of Chemistry 95:7, pages 744-750.
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Nadia Abed, Fatouma Saïd-Hassane, Fatima Zouhiri, Julie Mougin, Valérie Nicolas, Didier Desmaële, Ruxandra Gref & Patrick Couvreur. (2015) An efficient system for intracellular delivery of beta-lactam antibiotics to overcome bacterial resistance. Scientific Reports 5:1.
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Bin Zheng, Masano Sugiyama, Martin D. Eastgate, Alan Fritz, Saravanababu Murugesan & David A. Conlon. (2012) Development of a Process for the Preparation of Chloromethyl Chlorosulfate. Organic Process Research & Development 16:11, pages 1827-1831.
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David Rennison, Olivia Laita, Sergio Bova, Maurizio Cavalli, Brian Hopkins, Darwin S. Linthicum & Margaret A. Brimble. (2012) Design and synthesis of prodrugs of the rat selective toxicant norbormide. Bioorganic & Medicinal Chemistry 20:13, pages 3997-4011.
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Andrew IngramLouise ByersKaren FauldsBarry D. MooreDuncan Graham. (2008) SERRS-Based Enzymatic Probes for the Detection of Protease Activity. Journal of the American Chemical Society 130:36, pages 11846-11847.
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Carlos A. Velázquez, Qiao-Hong Chen, Michael L. Citro, Larry K. Keefer & Edward E. Knaus. (2008) Second-Generation Aspirin and Indomethacin Prodrugs Possessing an O 2 -(Acetoxymethyl)-1-(2-carboxypyrrolidin-1-yl)diazenium-1,2-diolate Nitric Oxide Donor Moiety: Design, Synthesis, Biological Evaluation, and Nitric Oxide Release Studies . Journal of Medicinal Chemistry 51:6, pages 1954-1961.
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Laurent Azéma, Christian Lherbet, Cécile Baudoin & Casimir Blonski. (2006) Cell permeation of a Trypanosoma brucei aldolase inhibitor: Evaluation of different enzyme-labile phosphate protecting groups. Bioorganic & Medicinal Chemistry Letters 16:13, pages 3440-3443.
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Joëlle Azéma, Brigitte Guidetti, Myriam Malet-Martino, Robert Martino & Christine Roques. (2006) Efficient approach to acyloxymethyl esters of nalidixic acid and in vitro evaluation as intra-ocular prodrugs. Bioorganic & Medicinal Chemistry 14:8, pages 2569-2580.
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Andrew M. Ingram, Kirsten Stirling, Karen Faulds, Barry D. Moore & Duncan Graham. (2006) Investigation of enzyme activity by SERRS using poly-functionalised benzotriazole derivatives as enzyme substrates. Organic & Biomolecular Chemistry 4:15, pages 2869.
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Ernst Binderup, Fredrik Björkling, Pernille Vig Hjarnaa, Scilla Latini, Bodil Baltzer, Morten Carlsen & Lise Binderup. (2005) EB1627: a soluble prodrug of the potent anticancer cyanoguanidine CHS828. Bioorganic & Medicinal Chemistry Letters 15:10, pages 2491-2494.
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Nicholas P. Power, Donald Bethell, Lee Proctor, Elliot Latham & Paul Dawson. (2004) Chloromethyl chlorosulfate: a new, catalytic method of preparation and reactions with some nucleophiles. Org. Biomol. Chem. 2:10, pages 1554-1562.
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Boguslaw Mudryk, Shanthi Rajaraman & Nachimuthu Soundararajan. (2002) A practical synthesis of chloromethyl esters from acid chlorides and trioxane or paraformaldehyde promoted by zirconium tetrachloride. Tetrahedron Letters 43:36, pages 6317-6318.
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Antti Mäntylä, Jouko Vepsäläinen, Tomi Järvinen & Tapio Nevalainen. (2002) A novel synthetic route for the preparation of alkyl and benzyl chloromethyl phosphates. Tetrahedron Letters 43:21, pages 3793-3794.
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H. Ouyang, R.T. Borchardt, T.J. Siahaan & D.G. Vander Velde. (2008) Synthesis and conformational analysis of a coumarinic acid‐based cyclic prodrug of an opioid peptide with modified sensitivity to esterase‐catalyzed bioconversion. The Journal of Peptide Research 59:4, pages 183-195.
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Hui Ouyang, Ronald T Borchardt & Teruna J Siahaan. (2002) Steric hindrance is a key factor in the coupling reaction of (acyloxy) alkyl-α-halides with phenols to make a new promoiety for prodrugs. Tetrahedron Letters 43:4, pages 577-579.
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Francisco Hernández-Luis, Alicia Hernández-Campos, Lilián Yépez-Mulia, Roberto Cedillo & Rafael Castillo. (2001) Synthesis and hydrolytic stability studies of albendazole carrier prodrugs. Bioorganic & Medicinal Chemistry Letters 11:11, pages 1359-1362.
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R. Alan Jones. 2001. Quaternary Ammonium Salts. Quaternary Ammonium Salts 69 118 .
Sai-hay Yiu & Edward E. Knaus. (1999) Synthesis of valproate, valerate, and 1-methyl-1, 4-dihydropyridyl-3-carbonyloxy ester derivatives of Hantzsch 1,4-dihydropyridines as potential prodrugs and their evaluation as calcium channel antagonist and anticonvulsant agents. Drug Development Research 48:1, pages 26-37.
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G. Brouillette, M. Kawamura, G.N. Kumar & N. Bodor. (1996) Soft Drugs. 21. Design and Evaluation of Soft Analogs of Propantheline. Journal of Pharmaceutical Sciences 85:6, pages 619-623.
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Gitte Juel Friis & Hans Bundgaard. (1996) Prodrugs of phosphates and phosphonates: Novel lipophilic α-acyloxyalkyl ester derivatives of phosphate- or phosphonate containing drugs masking the negative charges of these groups. European Journal of Pharmaceutical Sciences 4:1, pages 49-59.
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Lise Sylvest Nielsen, Frank Sløk & Hans Bundgaard. (1994) N-Alkoxycarbonyl prodrugs of mebendazole with increased water solubility. International Journal of Pharmaceutics 102:1-3, pages 231-239.
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Pascal Druzgala & Nicholas Bodor. (1991) Regioselective O-alkylation of cortienic acid and synthesis of a new class of glucocorticoids containing a 17α-alkoxy, a 17α-(1′-alkoxyethyloxy), a 17α-alkoxymethyloxy, or a 17α-methylthiomethyloxy function. Steroids 56:9, pages 490-494.
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B Loubinoux, JL Colin & V Thomas. (1991) Synthèse et activité biologique de prodrogues de l'acide oxolinique. European Journal of Medicinal Chemistry 26:4, pages 461-467.
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P. Druzgala, G. Hochhaus & N. Bodor. (1991) Soft drugs—10. Blanching activity and receptor binding affinity of a new type of glucocorticoid: Loteprednol etabonate. The Journal of Steroid Biochemistry and Molecular Biology 38:2, pages 149-154.
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Anne H. Kahns & Hans Bundgaard. (1990) Prodrugs as drug delivery systems. 107. Synthesis and chemical and enzymatic hydrolysis kinetics of various mono- and diester prodrugs of N-acetylcysteine. International Journal of Pharmaceutics 62:2-3, pages 193-205.
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E. BINDERUP & E. T. HANSEN. (2016) ChemInform Abstract: CHLOROSULFATES AS REAGENTS IN THE SYNTHESIS OF CARBOXYLIC ACID ESTERS UNDER PHASE‐TRANSFER CONDITIONS. Chemischer Informationsdienst 16:5.
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