Synthesis of the 2-amino-3, 5-diols (1-deoxy-5-hidroxysphingolipids)

Author(s)

Carla Cristina Perez

• Document type: Master's Dissertation
• Press: Campinas, SP.
• Institution: Universidade Estadual de Campinas (UNICAMP). Instituto de Química
• Defense date: 2008-02-20

Examining board members

Luiz Carlos Dias; Paulo Roberto Ribeiro Costa; Carlos Roque Duarte Correia

• Advisor: Luiz Carlos Dias

Abstract

We wish to describe here the diastereoselective reaction between chiral N-Boc-a-amino aldehydes and achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-a-amino alcohols in high diastereoselectivies. The 1,2-syn relative stereochemistry was determined after conversion of homoallylic alcohols to the corresponding N-Boc-oxazolidinones followed by analyses of the coupling constants in the H NMR spectra. Treatment of the homoallylic alcohols with catalytic amounts of OsO4 in the presence of NaIO4 provided the corresponding 4-N-Boc-amino-3-hydroxy ketones. It is very important to point out that, to the best of our knowledge, there was no useful and general approach to 4-N-Boc-amino-3-hydroxy ketones described in the literarure and this methodology stands as the most efficient approach to this class of compounds. Diastereoselective reduction of the 4-N-Boc-amino-3-hydroxy ketones provided the 1,3-syn and 1,3-anti aminodiols, respectively. The 1,3 relative stereochemistry was determined after C-NMR analyses of the corresponding isopropylidene acetals (AU)