A 3,4‐ trans ‐Fused Cyclic Protecting Group Facilitates α‐Selective Catalytic Synthesis of 2‐Deoxyglycosides | Zendy

Balmond Edward I. | Zendy; BenitoAlifonso David | Zendy; Coe Diane M. | Zendy; Alder Roger W. | Zendy; McGarrigle Eoghan M. | Zendy; Galan M. Carmen | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

A 3,4‐ trans ‐Fused Cyclic Protecting Group Facilitates α‐Selective Catalytic Synthesis of 2‐Deoxyglycosides

Author(s) -

Balmond Edward I.,

BenitoAlifonso David,

Coe Diane M.,

Alder Roger W.,

McGarrigle Eoghan M.,

Galan M. Carmen

Publication year - 2014

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201403543

Subject(s) - selectivity , disiloxane , chemistry , protecting group , catalysis , anomer , glycoconjugate , stereochemistry , combinatorial chemistry , side chain , organic chemistry , alkyl , biochemistry , polymer

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α‐selectivity and yields (77–97 %) using a trans ‐fused cyclic 3,4‐O‐disiloxane protecting group and TsOH⋅H 2 O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side‐chain conformation augments the selectivity.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research