Stereoselective Synthesis of α‐Keto‐deoxy‐ D ‐ glycero ‐ D ‐ galacto‐ nonulosonic Acid Glycosides by Means of the 4,5‐ O ‐Carbonate Protecting Group | Zendy

Crich David | Zendy; Navuluri Chandrasekhar | Zendy

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Stereoselective Synthesis of α‐Keto‐deoxy‐ D ‐ glycero ‐ D ‐ galacto‐ nonulosonic Acid Glycosides by Means of the 4,5‐ O ‐Carbonate Protecting Group

Author(s) -

Crich David,

Navuluri Chandrasekhar

Publication year - 2010

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.200907178

Subject(s) - stereoselectivity , protecting group , derivative (finance) , glycal , chemistry , glycoside , carbonate , stereochemistry , group (periodic table) , combinatorial chemistry , organic chemistry , catalysis , alkyl , financial economics , economics

Unrivaled : A 1‐adamantyl thioglycoside derivative of the nonulosonic acid KDN, carrying a 4,5‐ O ‐carbonate protecting group, is a highly efficient and α‐selective KDN donor when activated using N ‐iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). Glycosylations conducted with this protecting group do not suffer from competing glycal formation.

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