✦ LIBER ✦

Original loading and Suzuki conditions for the solid-phase synthesis of biphenyltetrazoles. Application to the first solid-phase synthesis of irbesartan

✍ Scribed by Nicolas Cousaert; Nicolas Willand; Jean-Claude Gesquière; André Tartar; Benoît Déprez; Rebecca Deprez-Poulain

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 132 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.02.147

No coin nor oath required. For personal study only.

✦ Synopsis

Biphenyltetrazoles are recognized privileged structures. Among them, the therapeutically important class of sartans displays antagonistic activity on AT1 receptors. We have developed a method for anchoring tetrazole derivatives via the heterocycle on a hydroxylated resin using zinc triflate. New Suzuki-Miyaura cross-coupling conditions are developed for the quantitative formation of the phenylphenyl bond. Our straightforward synthesis scheme, starting from the conserved phenyltetrazole moiety and ending with the appending of the structurally variable moiety, is well suited to the preparation of sartans and their analogues at a laboratory scale. We thus describe here the first solid phase synthesis of irbesartan, a marketed AT1 antagonist.

📜 SIMILAR VOLUMES

A simple linker for the attachment of al

A simple linker for the attachment of aldehydes to the solid phase. Application to solid phase synthesis by the multipin™ method

✍ Nicholas J. Ede; Andrew M. Bray 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 226 KB

A simple linker has been developed for the attachment of ahtehyde fimctionality. The aldehyde substrate is condensed with a support-bound serine or threonine to give an oxazolidine. The oxazolidine linker is stable to the conditions of Fntoc peptide synthesis, inchtding TFA treatment, but is cleaved

Solid phase synthesis of unsymmetrical s

Solid phase synthesis of unsymmetrical secondary amines—Application to the synthesis of arylethanolamines and arylpropanolamines

✍ Ashok V Purandare; Michael A. Poss 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 222 KB

A novel and simple solid phase synthesis ofunsymme~cal secondary amines was developed. The general methodology was applied to the synthesis of arylethanolamines and arylpropanolamines.

Efficient solid-phase synthesis of pepti

Efficient solid-phase synthesis of peptides with tripodal side-chain bridges and optimization of the solvent conditions for solid-phase cyclizations

✍ Wentao Zhang; John W. Taylor 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 256 KB

Solid-Phase Synthesis of Oligosaccharide

Solid-Phase Synthesis of Oligosaccharides: The Gateway to Glycobiology

✍ Bodo Eickhoff 📂 Article 📅 2004 🏛 John Wiley and Sons ⚖ 7 KB 👁 2 views

Solid-phase synthesis of N,N′-unsymmetri

Solid-phase synthesis of N,N′-unsymmetrically substituted ureas: application to the synthesis of carbaza peptides

✍ David Limal; Vincent Semetey; Pascal Dalbon; Michel Jolivet; Jean-Paul Briand 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 273 KB

The synthesis of Boc-or Fmoc-monoprotected propylenediamine derivatives is reported starting from N-protected a-amino acids. The introduction of these building blocks on solid support via the formation of a urea moiety leads to a new pseudopeptide family (Ca-CHe-CH~-Na(R)-CO-NH-Ca). Two carbonylati

The First Solid-Phase Synthesis of a Pep

The First Solid-Phase Synthesis of a Peptide-Tethered Platinum(II) Complex

✍ Marc S. Robillard; A. Rob P. M. Valentijn; Nico J. Meeuwenoord; Gijs A. van der 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 197 KB 👁 1 views