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Synthesis of Fmoc-Protected Arylphenylalanines (Bip Derivatives) via Nonaqueous Suzuki-Miyaura Cross-Coupling Reactions.
Qiao, Jennifer X; Fraunhoffer, Kenneth J; Hsiao, Yi; Li, Yi-Xin; Wang, Chunlei; Wang, Tammy C; Poss, Michael A.
Affiliation
  • Qiao JX; Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
  • Fraunhoffer KJ; Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
  • Hsiao Y; Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
  • Li YX; Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
  • Wang C; Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
  • Wang TC; Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
  • Poss MA; Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
J Org Chem ; 81(19): 9499-9506, 2016 10 07.
Article in En | MEDLINE | ID: mdl-27615449
ABSTRACT
A one-step synthesis of Fmoc-protected aryl/heteroaryl-substituted phenylalanines (Bip derivatives) using the nonaqueous palladium-catalyzed Suzuki-Miyaura cross-coupling (SMC) reaction of Fmoc-protected bromo- or iodophenylalanines is reported. This protocol allows for the direct formation of a variety of unnatural biaryl-containing amino acids in good to excellent yield, which can be readily used in subsequent Fmoc solid-phase peptide synthesis. The synthetic utility of this method is also demonstrated by the SMC reaction of bromophenylalanine-containing tripeptides.
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Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2016 Document type: Article Affiliation country: Publication country: EEUU / ESTADOS UNIDOS / ESTADOS UNIDOS DA AMERICA / EUA / UNITED STATES / UNITED STATES OF AMERICA / US / USA
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Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2016 Document type: Article Affiliation country: Publication country: EEUU / ESTADOS UNIDOS / ESTADOS UNIDOS DA AMERICA / EUA / UNITED STATES / UNITED STATES OF AMERICA / US / USA