Linked Life Data

14510358

Source:http://linkedlifedata.com/resource/pubmed/id/14510358

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
2003-9-26
pubmed:abstractText
The reaction mechanism of C-6 lithiation of uridine mediated by lithium hexamethyldisilazide (LiHMDS) has been investigated. LiHMDS alone dose not lithiate at C-6 of uridine. However, in the presence of an appropriate silylating agent, e.g. trimethylsilyl chloride, the reaction of 1 with LiHMDS allowed to lithiate at C-6 and gave the corresponding C-6 silylated product 2. The experimental results shown below revealed that O-4 (N-3) of uracil moiety may be temporarily masked by silylation, which triggers the C-6 lithiation by lowering the pKa of H-6. The reaction could efficiently be applied to the synthesis of 6,5'-C-cyclouridine, a nucleoside analogue fixed in a specific glycosyl torsion angle by a carbon-carbon bridge.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:author
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
17-8
pubmed:dateRevised
2006-11-30
pubmed:meshHeading
pubmed:year
2003
pubmed:articleTitle
Study on the reaction mechanism of C-6 lithiation of pyrimidine nucleosides by using lithium hexamethyldisilazide as a base.
pubmed:affiliation
School of Pharmaceutical Sciences, Showa University 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
pubmed:publicationType
Journal Article