Site‐ and Stereoselective Phosphoramidation of Carbohydrates Using a Chiral Catalyst and a Chiral Electrophile

• Published in: Advanced synthesis & catalysis Vol. 361; no. 16; pp. 3729 - 3732
• Main Authors: Glazier, Daniel A., Schroeder, John M., Blaszczyk, Stephanie A., Tang, Weiping
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.08.2019; Wiley Subscription Services, Inc
• Subjects: Biomolecules; carbohydrate; Carbohydrates; Catalysis; Catalysts; Chemical compounds; Chemistry; Chemistry, Applied; Chemistry, Organic; chiral catalyst; Chirality; Drugs; Functional groups; Natural products; organic catalysis; Organic chemistry; phosphoramidation; Physical Sciences; Science & Technology; site-selective; stereoselective; Stereoselectivity; Virulence; organic catalysis; phosphoramidation; chiral catalyst; site-selective; stereoselective; SELECTIVE FUNCTIONALIZATION; carbohydrate
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201900382

Carbohydrates are the most prevalent class of naturally occurring biomolecules. They mediate cell signaling, bacterial virulence, and metabolism, among other functions. The site‐selective functionalization of carbohydrates has been a long‐standing problem in chemistry. Phosphoramidates are a particularly challenging functional group to install stereoselectively because of the chirality at the phosphorus center. As such, the site‐ and stereoselective phosphoramidation of carbohydrates has never been achieved. We have developed the first site‐ and stereoselective phosphoramidation reaction of carbohydrates using a chiral catalyst and a chiral electrophile. This method offers a convenient solution for the selective synthesis of phosphoramidated carbohydrate‐containing prodrugs and natural products.