Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors | Zendy

Andrew B. Mayfield | Zendy; Jan B. Metternich | Zendy; Adam H. Trotta | Zendy; Eric N. Jacobsen | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors

Author(s) -

Andrew B. Mayfield,

Jan B. Metternich,

Adam H. Trotta,

Eric N. Jacobsen

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c00335

Subject(s) - chemistry , stereospecificity , anomer , thiourea , stereoselectivity , catalysis , stereochemistry , hydrogen bond , selectivity , substitution reaction , medicinal chemistry , organic chemistry , molecule

We report a new method for stereoselective O -furanosylation reactions promoted by a precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with an anomeric dialkylphosphate leaving group undergo substitution with high anomeric selectivity, providing access to the challenging 1,2- cis substitution pattern with a range of alcohol acceptors. A variety of stereochemically distinct, benzyl-protected glycosyl donors were engaged successfully as substrates. Mechanistic studies support a stereospecific mechanism in which rate-determining substitution occurs from a catalyst-donor resting-state complex.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research