| Phenylboronic acid esters of the common 2-deoxy-aldoses. | |
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MedLine Citation:
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PMID: 21816393 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Phenylboronic acid esters are formed by the three common 2-deoxy aldoses: 2-deoxy-d-erythro-pentose ('2-deoxy-d-ribose'), 2-deoxy-d-lyxo-hexose ('2-deoxy-d-galactose'), and 2-deoxy-d-arabino-hexose ('2-deoxy-d-glucose'). The major species that was formed from equimolar quantities of boronic acid and the aldose, was the 3,4-monoester of the pentopyranose in a skew-boat conformation, and the 4,6-monoester in the case of the two hexopyranoses. A double molar quantity of boronic acid led, for both 2-deoxy-hexoses, to the diester of the open-chain aldehydo isomer as the major product: the 3,5:4,6-diester for the lyxo-configured deoxy-hexose, and the 3,4:5,6-diester of the arabino-configured isomer. Minor products of all reactions were identified by a combined NMR/DFT methodology. |
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Authors:
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David Heß; Peter Klüfers |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-7-21 |
Journal Detail:
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Title: Carbohydrate research Volume: - ISSN: 1873-426X ISO Abbreviation: - Publication Date: 2011 Jul |
Date Detail:
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Created Date: 2011-8-5 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2011. Published by Elsevier Ltd. |
Affiliation:
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Ludwig-Maximilians-Universität, Department Chemie, Butenandtstraße 5-13, 81377 München, Germany. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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