C-glycosylation of oxygenated naphthols with 3-dimethylamino-2,3,6-trideoxy-L-arabino-hexopyranose and 3-azido-2,3,6-trideoxy-D-arabino-hexopyranose

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dc.contributor.author Brimble, MA en
dc.contributor.author Davey, RM en
dc.contributor.author McLeod, MD en
dc.contributor.author Murphy, M en
dc.date.accessioned 2011-09-19T01:44:02Z en
dc.date.issued 2003 en
dc.identifier.citation Australian Journal of Chemistry 56(8):787-794 2003 en
dc.identifier.issn 0004-9425 en
dc.identifier.uri http://hdl.handle.net/2292/8064 en
dc.description.abstract In connection with studies directed towards the synthesis of the pyranonaphthoquinone antibiotic medermycin, C-aryl glycosides were prepared by C-glycosylation of naphthols with glycosyl donors. Boron trifluoride diethyl etherate proved to be a suitable Lewis acid to promote the C-glycosylation, and use of the azido glycosyl donor proved more successful than using the dimethylamino glycosyl donor. 5-Hydroxy-1,4-dimethoxynaphthalene underwent facile C-glycosylation with two particular glycosyl donors, whereas 3-bromo-5-hydroxy-1,4-dimethoxynaphthalene was not an effective coupling partner with the same glycosyl donors. These studies indicate that subtle steric and electronic effects need to be considered in order to fine-tune C-glycosylations when using highly functionalized glycosyl donors. en
dc.language EN en
dc.relation.ispartofseries Australian Journal of Chemistry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0936-5214/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject ANTIBIOTICS en
dc.subject REVISION en
dc.subject ANALOGS en
dc.subject ROUTE en
dc.title C-glycosylation of oxygenated naphthols with 3-dimethylamino-2,3,6-trideoxy-L-arabino-hexopyranose and 3-azido-2,3,6-trideoxy-D-arabino-hexopyranose en
dc.type Journal Article en
dc.identifier.doi 10.1071/CH02236 en
pubs.issue 8 en
pubs.begin-page 787 en
pubs.volume 56 en
dc.rights.holder Copyright: 2003 CSIRO en
pubs.end-page 794 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 6163 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en

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