A new strategy for the synthesis of taurine derivatives using the 'safety-catch' principle for the protection of sulfonic acids.

  title={A new strategy for the synthesis of taurine derivatives using the 'safety-catch' principle for the protection of sulfonic acids.},
  author={Sonja Seeberger and R. Griffin and I. Hardcastle and B. Golding},
  journal={Organic \& biomolecular chemistry},
  volume={5 1},
The safety-catch principle has been applied for the development of a new method for protecting sulfonic acids. 2,2-Dimethylsuccinic acid was reduced to 2,2-dimethylbutane-1,4-diol, which was selectively silylated to give 4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutan-1-ol. Reaction of the latter compound with 2-chloroethanesulfonyl chloride in the presence of triethylamine afforded 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutyl ethenesulfonate directly. The ethenesulfonate underwent… Expand
11 Citations
Chapter 5.3 Five-membered ring systems: Furans and benzofurans
Publisher Summary This chapter reviews papers that were published in 2006 on the reactions and syntheses of furans, benzofurans, and their derivatives. Like 2005, many new naturally occurringExpand
An oxidatively-activated safety catch linker for solid phase synthesis.
A N-benzyl-4-amino-2,2-dimethylbutanoic acid-based system has been developed as a new oxidatively activated safety catch linker for reaction monitoring and optimisation on solid support. The CANExpand
Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(III) EuroTracker® dyes.
The synthesis is described of a series of meta and para-substituted phenylsulfonate derivatives of very bright Eu(III) complexes with arylphosphinate groups and strongly absorbing aryLalkynylpyridine moieties, which exhibit enhanced water solubility and photophysical properties not perturbed significantly by introduction of the anionic sulfonate groups. Expand
A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore.
The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatography. Expand
Taurine isothiocyanate: a versatile intermediate for the preparation of ureas, thioureas, and guanidines. Taurine-derived cyclodextrins
A versatile and expeditious synthesis of taurine-derived thioureas, ureas, and guanidines using taurine isothiocyanate as the key intermediate is reported. Thioureas were obtained by a one-potExpand
Synthesis and solid-phase purification of anthranilic sulfonamides as CCK-2 ligands.
A novel strategy for the synthesis of cholecystokinin-2 receptor ligands was developed. The route employs a solution-phase synthesis of a series of anthranilic sulfonamides followed by a resinExpand
Design and application of esterase-labile sulfonate protecting groups.
Three esterase-labile, but chemically-stable sulfonate protecting groups have been designed and synthesized and one of them allowed the cytoplasmic delivery and unmasking of a sulfonated dye in live cells. Expand
Designed to dissolve: suppression of colloidal aggregation of Cu(I)-selective fluorescent probes in aqueous buffer and in-gel detection of a metallochaperone.
Due to the lipophilicity of the metal-ion receptor, previously reported Cu(I)-selective fluorescent probes form colloidal aggregates, as revealed by dynamic light scattering. To address this problem,Expand
New synthetic strategies for acyclic and cyclic pyrimidinethione nucleosides and their analogues
Pyrimidinethione nucleosides are effective compounds and have significant and pivotal effects in several fields and new synthetic strategies including acyclic and cyclic derivatives have been reported. Expand


Novel Route to Sulfonated Polyphosphazenes: Single-Step Synthesis Using “Noncovalent Protection” of Sulfonic Acid Functionality
A single-step approach for the synthesis of polyphosphazenes containing sulfonic acid functionalities is developed. Polyphosphazene “sulfonation” is conducted via the direct replacement of chlorineExpand
Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.
Many currently known antagonists for P2 purinergic receptors are anionic molecules bearing one or several phenylsulfonate groups. Among the P1 (adenosine) receptor antagonists, the xanthineExpand
Intramolecular Diels−Alder Reactions Using α-Methylene Lactones as Dienophile
Several dienals were prepared and reacted in the presence of zinc metal with ethyl 2-bromomethylacrylate to provide in a Reformatsky-like reaction α-methylene lactones carrying a dienyl side chain.Expand
Abstract The isobutyl ester proved to be a useful protecting group for the construction of sulfonate-containing analogs of nucleosides. The syntheses of useful uridine or adenosineExpand
Exploiting Differences in Solution vs Solid-Supported Reactivity for the Synthesis of Sulfonic Acid Derivatives
We describe a method herein for the protection of aryl and alkyl sulfonates during synthesis which employs commercially available Wang or MBOH resin, both of which terminate as benzyl alcohols, asExpand
Investigation of subsite preferences in aminopeptidase A (EC led to the design of the first highly potent and selective inhibitors of this enzyme.
These first described highly potent inhibitors of aminopeptidase A could allow studies about the role of physiological substrates of APA such as angiotensin II and cholecystokinin CCK(8) in the central nervous system. Expand
Pentafluorophenyl sulfonate ester as a protecting group for the preparation of biaryl- and heterobiaryl sulfonate esters.
The use of the pentafluorophenyl (PFP) group as a sulfonic acid protecting group has allowed the synthesis of new biaryl- and heterobiaryl-PFP-sulfonate esters by use of a novel inorganic base, anhydrous sodium tetraborate. Expand
2,5-dimethylphenacyl esters: a photoremovable protecting group for phosphates and sulfonic acids.
2,5-Dimethylphenacyl phosphoric and sulfonic esters release the corresponding acids upon irradiation in nearly quantitative isolated yields, with quantum yields phi = 0.71 and 0.68 in methanol, 0.09Expand
A comprehensive approach to the synthesis of sulfate esters.
The exceptionally stable neopentyl protecting group and the labile isobutylprotect group were utilized in the synthesis of aromatic and aliphatic sulfate monoesters. Expand
Neopentyl ester protecting groups for arylsulfonic acids
Abstract We report that neopentylsulfonate esters are stable to a variety of standard organic reaction conditions and are easily cleaved to sulfonic acids. We also discuss the use ofExpand