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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

Brimble, Margaret A; Davey, Roger M; McLeod, Malcolm; Murphy, Maureen


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...[Show more]

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH02236


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