A Convenient Synthesis of Pyrano[2,3-b][1,5]oxazepines by Ring Closure of O-Glycosyl Amino Acids

✍ Scribed by Ahmed I. Khodair; Richard R. Schmidt

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 365 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201101148

✦ Synopsis

Abstract

N‐Boc‐protected serine and threonine esters could be readily added to 2‐nitroglycals, affording exclusively α‐ and β‐anomers with galacto‐ and gluco‐configuration, respectively. Nitro group reduction to the amino group and also ester cleavage led to compounds 2, 6, and 11, which can be regarded as dipeptide mimetics. From these compounds, bicyclic pyrano[2.3‐b][1,5]oxazepines 7–14 were prepared by ring closure.