Document Detail

Stereoselective synthesis of 2,3-diamino-2,3-dideoxy-beta-D-mannopyranosyl uronates.
MedLine Citation:
PMID:  21793528     Owner:  NLM     Status:  Publisher    
With the aim to find an efficient synthetic procedure for the construction of 2,3-diamino-2,3-dideoxy-beta-D-mannuronic acids we evaluated three mannosyl donors: S-phenyl 4,6-di-O-acetyl-2,3-diazido mannopyranoside, S-phenyl 2,3-diazido-4,6-O-benzylidene mannopyranoside and S-phenyl 2,3-diazido mannopyranosyl methyl uronate. The first two mannosylating agents are rather unselective or slightly alpha-selective in their condensation with three different acceptors. The mannuronic acid donor on the other hand reliably provides the desired beta-mannosidic linkage. A mechanistic rationale is put forward to account for the different behavior of the three donor types. Suitably protected 2,3-diazido mannuronic acids were employed to construct the all-cis linked tetrasaccharide repeating unit of the capsular polysaccharide of Bacillus stearothermophilus, featuring two 2,3-diacetamido-2,3-dideoxy-beta-D-mannuronic acids.
Marthe T C Walvoort; Gert-Jan Moggré; Gerrit Lodder; Herman S Overkleeft; Jeroen Dirk Cornelis Codée; Gijsbert A van der Marel
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-7-27
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-7-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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