Attributes | Values |
---|
rdf:type
| |
Description
| - We describe a polymer-supported stereoselective synthesis of the (1S,5S)-6-oxa-3,8-biazabicyclooctane-bridged scaffold by tandem iminium ion cyclization/nucleophilic addition reactions. A series of resin-bound acyclic intermediates bearing different substituents were prepared, and the scope and limitations of the chemical route leading to the bridged scaffold were evaluated. The Thr-derived bridged scaffold was found to be substantially more stable in acid than the Ser-derived scaffold, which was partially transformed into dihydropyrazinones. Substitution at the iminium-forming nitrogen was critical for acid stability, and the N-arylsulfonamides with electron-withdrawing groups yielded the highest purity of the crude products prepared by acid-mediated cleavage. The acid-labile target compounds were synthesized by nucleophile-mediated cleavage from the esterified Wang resin and cyclization in formic acid.
- We describe a polymer-supported stereoselective synthesis of the (1S,5S)-6-oxa-3,8-biazabicyclooctane-bridged scaffold by tandem iminium ion cyclization/nucleophilic addition reactions. A series of resin-bound acyclic intermediates bearing different substituents were prepared, and the scope and limitations of the chemical route leading to the bridged scaffold were evaluated. The Thr-derived bridged scaffold was found to be substantially more stable in acid than the Ser-derived scaffold, which was partially transformed into dihydropyrazinones. Substitution at the iminium-forming nitrogen was critical for acid stability, and the N-arylsulfonamides with electron-withdrawing groups yielded the highest purity of the crude products prepared by acid-mediated cleavage. The acid-labile target compounds were synthesized by nucleophile-mediated cleavage from the esterified Wang resin and cyclization in formic acid. (en)
|
Title
| - Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes
- Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes (en)
|
skos:prefLabel
| - Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes
- Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes (en)
|
skos:notation
| - RIV/61989592:15310/13:33147692!RIV14-GA0-15310___
|
http://linked.open...avai/predkladatel
| |
http://linked.open...avai/riv/aktivita
| |
http://linked.open...avai/riv/aktivity
| - P(EE2.3.20.0009), P(GAP207/12/0473), P(ME09057)
|
http://linked.open...iv/cisloPeriodika
| |
http://linked.open...vai/riv/dodaniDat
| |
http://linked.open...aciTvurceVysledku
| |
http://linked.open.../riv/druhVysledku
| |
http://linked.open...iv/duvernostUdaju
| |
http://linked.open...titaPredkladatele
| |
http://linked.open...dnocenehoVysledku
| |
http://linked.open...ai/riv/idVysledku
| - RIV/61989592:15310/13:33147692
|
http://linked.open...riv/jazykVysledku
| |
http://linked.open.../riv/klicovaSlova
| - Bicyclic compounds; Solid-phase synthesis; Nucleophilic addition; Heterocycles; Peptidomimetics (en)
|
http://linked.open.../riv/klicoveSlovo
| |
http://linked.open...odStatuVydavatele
| - DE - Spolková republika Německo
|
http://linked.open...ontrolniKodProRIV
| |
http://linked.open...i/riv/nazevZdroje
| - European Journal of Organic Chemistry
|
http://linked.open...in/vavai/riv/obor
| |
http://linked.open...ichTvurcuVysledku
| |
http://linked.open...cetTvurcuVysledku
| |
http://linked.open...vavai/riv/projekt
| |
http://linked.open...UplatneniVysledku
| |
http://linked.open...v/svazekPeriodika
| |
http://linked.open...iv/tvurceVysledku
| - Krchňák, Viktor
- Zajíček, Jaroslav
- Schütznerová, Eva
- Oliver, Allen G
|
http://linked.open...ain/vavai/riv/wos
| |
issn
| |
number of pages
| |
http://bibframe.org/vocab/doi
| |
http://localhost/t...ganizacniJednotka
| |