Efficient stereoselective synthesis of 5a-carba-α-L-mannopyranose starting from naturally abundant (−)-shikimic acid

Abstract

In this article, an efficient and practical stereoselective synthesis of 5a-carba-α-L-mannopyranose from naturally abundant (−)-shikimic acid is discussed. 5a-Carba-α-L-mannopyranose was synthesized via 11 steps in 43% overall yield starting from (−)-shikimic acid. The overall yield of the total synthesis is high, the reaction conditions for all steps are mild, the operation procedures of all steps are simple, and the reagents used in all steps are cheap and readily available.

Graphical Abstract

Keywords:

• Carbasugar
• mannopyranose
• pseudo-sugar
• shikimic acid
• synthesis

Additional information

Funding

This work was financially supported by the National Natural Science Foundation of China [20972048, 20172015].