| Stereoselective synthesis of 2,3-diamino-2,3-dideoxy-beta-D-mannopyranosyl uronates. | |
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MedLine Citation:
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PMID: 21793528 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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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:
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Type: JOURNAL ARTICLE Date: 2011-7-27 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 Jul |
Date Detail:
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Created Date: 2011-7-28 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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