Document Detail


Preparation of 2,6-anhydro-aldose acylhydrazones, -semicarbazones and -oximes from 2,6-anhydro-aldononitriles (glycosyl cyanides).
MedLine Citation:
PMID:  12791286     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Reductive transformation of per-O-acylated 2,6-anhydro-aldononitriles (glycopyranosyl cyanides of the D-galacto, D-gluco, D-xylo, and D-arabino configuration) with Raney-nickel-NaH(2)PO(2) in pyridine-AcOH-water solvent mixture in the presence of benzoylhydrazine, ethyl carbazate, and semicarbazide gave the corresponding anhydro-aldose benzoylhydrazones, -ethoxycarbonylhydrazones, and -semicarbazones, respectively. Acid catalyzed transimination of the semicarbazones with thiosemicarbazide, hydroxylamine, and O-benzylhydroxylamine, resulted in the formation of anhydro-aldose thiosemicarbazones, and E/Z mixtures of anhydro-aldose oximes, and O-benzyl-(anhydro-aldose)-oximes, respectively.
Authors:
Marietta Tóth; László Somsák
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Carbohydrate research     Volume:  338     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2003 Jun 
Date Detail:
Created Date:  2003-06-06     Completed Date:  2004-03-11     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  1319-25     Citation Subset:  IM    
Affiliation:
Department of Organic Chemistry, University of Debrecen, H-4010, P.O. Box 20, Debrecen, Hungary.
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MeSH Terms
Descriptor/Qualifier:
Acids / chemistry
Azo Compounds / chemical synthesis
Catalysis
Glycosides / chemical synthesis
Glycosylation
Hydrazones / chemical synthesis*,  chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Structure
Nitriles / chemistry*
Oximes / chemical synthesis*,  chemistry
Semicarbazones / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Acids; 0/Azo Compounds; 0/Glycosides; 0/Hydrazones; 0/Nitriles; 0/Oximes; 0/Semicarbazones

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