Linked Life Data

17388629

Source:http://linkedlifedata.com/resource/pubmed/id/17388629

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
9
pubmed:dateCreated
2007-4-20
pubmed:abstractText
In our efforts to design new anti-cancer vaccines based on the tumor associated carbohydrate antigen dimeric Lex, we have synthesized the fragment GlcNAc-beta-(1-->3)-Gal-beta-(1-->4)-GlcNAc-beta-(1-->O)-Me. Although it is notoriously difficult to chemically protect the primary OH groups in beta-lactoside derivatives, a 6,6'-disilylated intermediate was prepared in 82% yield. It was converted to a glycosyl acceptor free at O-3' that was glycosylated with a 2-deoxy-2-phthalimido trichloroacetimidate glucosyl donor. This glycosylation required large amounts of TMSOTf to proceed. Such conditions led to the formation of a Ferrier rearrangement glycosylation product. Despite these hurdles, the desired trisaccharide was isolated in 53% yield and easily deprotected in four steps.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Apr
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
27
pubmed:volume
72
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
3585-8
pubmed:meshHeading
pubmed:year
2007
pubmed:articleTitle
Selective protection of 2-azido-lactose and in situ Ferrier rearrangement during glycosylation: synthesis of a dimeric Lewis X fragment.
pubmed:affiliation
Department of Chemistry, University of Guelph, Guelph, Ontario N1G 2W1, Canada.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't