Synthesis and Conformational Analysis of the First 3-Oxa-7-thia-1- r-azabicyclo[3.3.0]-c-5-octane Single Functionalised at the C-5 Position

Andrada      But; Pedro      Lameiras; Ioan      Silaghi-Dumitrescu; Carmen      Batiu; Sophie      Guillard; Yvan      Ramondenc; Mircea      Darabantu

Letters in Organic Chemistry

Author(s): Andrada But, Pedro Lameiras, Ioan Silaghi-Dumitrescu, Carmen Batiu, Sophie Guillard, Yvan Ramondenc and Mircea Darabantu

DOI: 10.2174/157017810791130658

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Synthesis and Conformational Analysis of the First 3-Oxa-7-thia-1- r-azabicyclo[3.3.0]-c-5-octane Single Functionalised at the C-5 Position

Page: [283 - 290] Pages: 8

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Abstract

Starting from TRIS [2-amino-2-(hydroxymethyl)propane-1,3-diol] via its thia analogue, 2-amino-2- (mercaptomethyl)propane-1,3-diol double cyclocondensation with formaldehyde, we report a four steps synthesis of the first term in the title series of compounds, bearing the exploitable hydroxymethyl functionality at the C-5 position. Conformational analysis is discussed based on DFT calculations and 1H-DNMR.

Keywords: Cysteinols, 1,3-oxazolines, NMR, serinols, thionation

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