A Novel Base‐Induced Isomerization Gives Access to Unprecedented ( E )‐ exo ‐Glycals | Zendy

Eppe Guillaume | Zendy; Dumitrescu Lidia | Zendy; Pierrot Olivier | Zendy; Li Tianlei | Zendy; Pan Weidong | Zendy; Vincent Stéphane P. | Zendy

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A Novel Base‐Induced Isomerization Gives Access to Unprecedented ( E )‐ exo ‐Glycals

Author(s) -

Eppe Guillaume,

Dumitrescu Lidia,

Pierrot Olivier,

Li Tianlei,

Pan Weidong,

Vincent Stéphane P.

Publication year - 2013

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201300969

Subject(s) - isomerization , scope (computer science) , computer science , chemistry , service (business) , base (topology) , mechanism (biology) , world wide web , combinatorial chemistry , information retrieval , stereochemistry , organic chemistry , catalysis , business , mathematics , philosophy , epistemology , mathematical analysis , marketing , programming language

Bump the base : This study reports the discovery of the base‐induced Z ‐to‐ E isomerization of exo ‐glycals bearing an electron‐withdrawing group (EWG). The scope of this novel transformation regarding the carbohydrate unit is also discussed. After elucidating the mechanism, preparation of novel ( E )‐ exo ‐ glycals was performed (TBS= tert ‐butyldimethylsilyl).

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