Source:http://linkedlifedata.com/resource/pubmed/id/18954866
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
18
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pubmed:dateCreated |
2008-11-10
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pubmed:abstractText |
An efficient synthesis of 4-methoxyphenyl alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->2)-6-deoxy-alpha-L-Talp, the tetrasaccharide related to the GPLs of Mycobacterium intracellare serotype 7, was achieved with 4-methoxyphenyl 3,4-di-O-benzoyl-6-deoxy-alpha-L-talopyranoside (6c) as the key intermediate which was obtained through selective 3-O-benzoylation of 4-O-benzoyl-6-deoxy-alpha-L-taloside. Coupling of 6c with 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate followed by removal of the allyloxycarbonyl protecting group afforded the disaccharide acceptor 11. Condensation of 11 with 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1-->3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate and subsequent deprotection gave the target tetrasaccharide.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/6-deoxytalose,
http://linkedlifedata.com/resource/pubmed/chemical/Deoxy Sugars,
http://linkedlifedata.com/resource/pubmed/chemical/Glycolipids,
http://linkedlifedata.com/resource/pubmed/chemical/Hexoses,
http://linkedlifedata.com/resource/pubmed/chemical/Oligosaccharides
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pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
1873-426X
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pubmed:author | |
pubmed:issnType |
Electronic
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pubmed:day |
8
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pubmed:volume |
343
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
3107-11
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pubmed:meshHeading |
pubmed-meshheading:18954866-Acylation,
pubmed-meshheading:18954866-Carbohydrate Sequence,
pubmed-meshheading:18954866-Deoxy Sugars,
pubmed-meshheading:18954866-Glycolipids,
pubmed-meshheading:18954866-Hexoses,
pubmed-meshheading:18954866-Molecular Sequence Data,
pubmed-meshheading:18954866-Mycobacterium avium Complex,
pubmed-meshheading:18954866-Oligosaccharides,
pubmed-meshheading:18954866-Substrate Specificity
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pubmed:year |
2008
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pubmed:articleTitle |
Synthesis of the 6-deoxytalose-containing tetrasaccharide of the glycopeptidolipid from Mycobacterium intracellare serotype 7.
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pubmed:affiliation |
Key Lab of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100094, China.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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