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Phenylboronic acid esters of the common 2-deoxy-aldoses.
MedLine Citation:
PMID:  21816393     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
David Heß; Peter Klüfers
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-7-21
Journal Detail:
Title:  Carbohydrate research     Volume:  -     ISSN:  1873-426X     ISO Abbreviation:  -     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-8-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011. Published by Elsevier Ltd.
Affiliation:
Ludwig-Maximilians-Universität, Department Chemie, Butenandtstraße 5-13, 81377 München, Germany.
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