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

Article abstract of DOI:10.2174/157017810791130658

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.