Concise and divergent approach to 3- O-acyl- l-noviose derivatives and their 3-amino bioisosteres: 3- O-benzoyl- l-noviose and N-benzoyl-3-amino- l-noviose

Abstract

Generally applicable concise approaches to 3- O-acyl- l-noviose derivatives and their 3-amino bioisosteres, represented by 5 and 6, were described. Chiral aldehyde 7 was thus prepared from dimethyl l-tartrate in five steps, and converted into 5 and 6 by employing substrate induced asymmetric aldehyde or N-sulfinyl aldimine allylation and dihydropyrane epoxidation as key steps, respectively.