An efficient and practical chemo-enzymatic route to (3R,3aR,6R,6aR)-hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-aminoisomannide) from renewable sources

Valerio Zullo, Antonella Petri, Anna Iuliano
2021 SynOpen  
The synthesis of 6-aminoisomannide is easily achieved starting from the renewable, inexpensive and commercially available isosorbide, in 66% overall yield. A biocatalysed highly regioselective acetylation of the 3-endo hydroxyl group of isosorbide was followed by the stereospecific interconversion of the 6-exo hydroxyl group into azido group, through reaction with trifluoromethanesulfonic anhydride followed by nucleophilic displacement of the triflate group by sodium azide. Finally, reduction
more » ... the azido group and deacetylation of the 3-hydroxy group were performed one pot by using LiAlH4.
doi:10.1055/a-1532-5825 fatcat:uddbkfl24rbz7njdfi4uefilca