Literature DB >> 11428032

Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol.

L Bunch1, P O Norrby, K Frydenvang, P Krogsgaard-Larsen, U Madsen.   

Abstract

[figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.

Entities:  

Mesh：

Substances：

Year:  2001        PMID： 11428032     DOI： 10.1021/ol0069397

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Discovery of a new class of ionotropic glutamate receptor antagonists by the rational design of (2S,3R)-3-(3-carboxyphenyl)-pyrrolidine-2-carboxylic acid.

Authors:  Ann M Larsen; Raminta Venskutonytė; Elena Antón Valadés; Birgitte Nielsen; Darryl S Pickering; Lennart Bunch
Journal:  ACS Chem Neurosci       Date:  2010-11-12       Impact factor: 4.418

2.  An Alkoxide Anion Triggered tert-Butyloxycarbonyl Group Migration. Mechanism and Application.

Authors:  Fengtian Xue; Richard B Silverman
Journal:  Tetrahedron Lett       Date:  2010-05-05       Impact factor: 2.415

3.  An RCM strategy to stereodiverse delta-sultam scaffolds.

Authors:  María Jiménez-Hopkins; Paul R Hanson
Journal:  Org Lett       Date:  2008-05-01       Impact factor: 6.005
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.