Document Detail

The Amadori rearrangement as key reaction for the synthesis of neoglycoconjugates.
MedLine Citation:
PMID:  18346717     Owner:  NLM     Status:  MEDLINE    
The Amadori rearrangement was introduced as a key step for the conjugation of carbohydrate moieties with suitable amines such as aliphatic amines and amino acid derivatives. The rearrangement products were further transformed into the corresponding 1-N,2-O cyclic carbamates employing triphosgene to obtain anomerically stable glycoconjugates. The reaction conditions were probed on a model substrate, 3,5-di-O-benzyl-alpha,beta-d-glucofuranose and further applied to d-glycero-d-gulo-heptose, which gave 'd-gluco-conjugates' in the alpha-anomeric form exclusively in high isolated yields.
Tanja M Wrodnigg; Christiane Kartusch; Carina Illaszewicz
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-03-02
Journal Detail:
Title:  Carbohydrate research     Volume:  343     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2008 Aug 
Date Detail:
Created Date:  2008-06-23     Completed Date:  2008-10-06     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  2057-66     Citation Subset:  IM    
Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
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MeSH Terms
Glycoconjugates / chemical synthesis*
Reg. No./Substance:

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