Convenient Synthesis of Bicyclic Carbohydrate 1,2‐Lactones and Their Stereoselective Opening to 1‐Functionalized Glucose Derivatives | Zendy

Yin Jian | Zendy; Linker Torsten | Zendy

Premium

Convenient Synthesis of Bicyclic Carbohydrate 1,2‐Lactones and Their Stereoselective Opening to 1‐Functionalized Glucose Derivatives

Author(s) -

Yin Jian,

Linker Torsten

Publication year - 2008

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.200802178

Subject(s) - stereoselectivity , decarboxylation , carbohydrate , chemistry , bicyclic molecule , anomer , stereochemistry , organic chemistry , combinatorial chemistry , catalysis

Closed and re‐opened for business : C‐2 branched carbohydrates 1 cyclize under conditions of decarboxylation to the hitherto unknown carbohydrate 1,2‐lactones 2 in high yields. The gluco isomer can be opened at the anomeric position with various nuceophiles in the presence of Sc(OTf) 3 , which allows the stereoselective synthesis of 1‐functionalized glucose derivatives 3 . Thus, 1,2‐ bis‐C ‐branched saccharides become available in only a few steps starting from glycals.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research