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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
2
|
pubmed:dateCreated |
1998-6-2
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pubmed:abstractText |
A concise practical, large scale-adaptable six-step sequence has been developed for the transformation of diacetone-glucose into 4,6-di-O-benzoyl-3-O-benzyl-alpha-D-arabino-hexopyranos-2-ulosy l bromide (7), a most useful indirect beta-D-mannosyl donor as its blocking group pattern allows the construction of biologically relevant beta-D-mannosides branched at O-3 and O-6. The broad utility of this new ulosyl bromide 7 resides in its high anomeric reactivity, and in the ease and uniformity with which beta-stereocontrol can be achieved over both, glycosidations and carbonyl reduction of the beta-ulosides formed: Koenigs-Knorr conditions exclusively provide beta-glycosiduloses, hydride reduction of their carbonyl functions proceeds with high stereoselectivities (> 20:1) in favor of the beta-D-mannosides. These preparatively auspicious properties are materialized in an efficient, straightforward synthesis of alpha-D-Manp-(1-->6)-[alpha-D-Manp-(1-->3)]-beta-D-Manp++ +-(1-->O)-Octyl, the 3,6-O-branched core-mannotrioside carrying an octyl spacer instead of the chitobiosyl unit.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
0008-6215
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
305
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pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
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pubmed:pagination |
293-303
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading | |
pubmed:year |
1997
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pubmed:articleTitle |
4,6-di-O-benzoyl-3-O-benzyl-alpha-D-arabino-hexo-pyranos-2-ulosyl bromide: a conveniently accessible glycosyl donor for the expedient construction of diantennary beta-D-mannosides branched at O-3 and O-6.
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pubmed:affiliation |
Institut für Organische Chemie, Technische Universität Darmstadt, Germany.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
|