Electrophilic Amination as a Route to Deoxyamino Sugars: Synthesis of the Key Intermediate for 1β-Methylcarbapenem

Article abstract of DOI:10.1021/jo00244a061

The application of electrophilic amination of keto sugars as a route to deoxyamino sugars by the reaction of sugar enolates with dibenzyl azodicarboxylate has been explored.Although the success of the reaction is dependent on several factors, such as the location of the carbonyl group and the substitution pattern on the pyranosidulose ring, the process is synthetically promising.This has been demonstrated by preparation of the protected Melillo Lactone analogue 18, a key intermediate for 1β-methylcarbapenem.