Linked Life Data

17337343

Source:http://linkedlifedata.com/resource/pubmed/id/17337343

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
9
pubmed:dateCreated
2007-4-2
pubmed:abstractText
Tricarbonylation of clarithromycin has been effected in a one-pot reaction with phosgene. The 11,12-diol moiety was closed into a cyclic carbonate, while the dimethylamino alcohol of the desosamine sugar was cyclised with loss of a methyl group to form a cyclic 2',3'-carbamate. The 4'' hydroxyl group in clarithromycin was converted into a chloroformate group and subsequently to an allyl carbonate which on Pd-catalysis furnished a novel N-demethylclarithromycin 2',3'-carbamate-11,12-carbonate. Hydrolytic removal of the cladinose sugar and a subsequent oxidation furnished the corresponding ketolide. The 11,12-cyclic carbonate moiety was cleaved by sodium azide to the 10,11-anhydro-9-ketone. 11-N-Arylated cyclic 11,12:2',3'-dicarbamate derivatives were prepared in a copper(I) chloride aided reaction between aryl isocyanates and 10,11-anhydro 9-ketones. The products are novel N-arylated-N'-demethylated 11,12:2',3'-dicarbamate ketolides derived from clarithromycin.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
May
pubmed:issn
0968-0896
pubmed:author
pubmed:issnType
Print
pubmed:day
1
pubmed:volume
15
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
3266-77
pubmed:meshHeading
pubmed:year
2007
pubmed:articleTitle
Preparation of cyclic 2',3'-carbamate derivatives of erythromycin macrolide antibiotics.
pubmed:affiliation
Department of Chemistry, University of Oslo, N-0315 Oslo, Norway.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't