Amino sugars are key structural features present in various natural products, which are central to their biological activity. Examples of such natural products include the antibiotics vancomycin and erythromycin, whose amino sugars vancosamine and desosamine mediate aqueous solubility and ribosome binding, respectively. Our group has previously synthesized 2-aminoseptanosides from pyranoses via vinyl Grignard addition, ozonolysis, and cyclization. Our goal is to continue to move the amine around the ring in order to expand this method and to determine what effect it may have on activity. Here we show the synthesis of 3-aminoseptanosides from furanoses via allyl Grignard addition, ozonolysis, and cyclization. The new 3-amino septanosides were synthesized to contain different reactive handles at the aglycone position in order to allow for post-glycosylation modification strategies to be implemented for further diversification.

Synthesis and diversification of 3-aminoseptanosides from furanoses

Macromolecular Chemistry: The Second Century

[Author Benefits](https://scimeetings.acs.org/?utm_source=pubs_content_marketing&utm_medium=website&utm_campaign=0320_MCF_NPI_Launch_Spring_Homepage&ref=pubs_content_marketing)

[How to use SciMeetings](https://storage.googleapis.com/dl.morressier.com/acs/SciMeetings-ACSSpring2020-HowToGuide_M3020-Final.pdf)

[Frequently Asked Questions](https://storage.googleapis.com/dl.morressier.com/acs/SciMtng_ACSNMSp2020_FAQ_M3120_Final.pdf)

ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.