Stereoselective Cyclopropanation in the Synthesis of 3′-Deoxy-3′‑C‑hydroxymethyl-2′,3′-methylene-uridine

The synthesis of the novel 2′,3′-cyclopropane nucleoside 3′-deoxy-3′-C-hydroxymethyl-2′,3′-methylene-uridine is described. Stereoselective construction of the cyclopropane ring was achieved via Simmons–Smith cyclopropanation of a benzyl protected silyl enol ether, which was itself derived from 1,2-O...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 18; pp. 4878 - 4880
Main Authors Komsta, Zofia, Mayes, Benjamin A, Moussa, Adel, Shelbourne, Montserrat, Stewart, Alistair, Tyrrell, Andrew J, Wallis, Laura L, Weymouth-Wilson, Alexander C, Yurek-George, Alexander
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.09.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclopropanes - chemistry
Molecular Structure
Monosaccharides - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Uridine - analogs & derivatives
Uridine - chemical synthesis
Uridine - chemistry
Uridine - pharmacology
SYSTEM
ACID
HIV
ANALOGS
PYRIMIDINE NUCLEOSIDES
ANTIVIRAL ACTIVITY
AGENTS
INHIBITORS
NUCLEOSIDE SYNTHESIS
SCAFFOLD
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Summary:The synthesis of the novel 2′,3′-cyclopropane nucleoside 3′-deoxy-3′-C-hydroxymethyl-2′,3′-methylene-uridine is described. Stereoselective construction of the cyclopropane ring was achieved via Simmons–Smith cyclopropanation of a benzyl protected silyl enol ether, which was itself derived from 1,2-O-isopropylidene-α-d-xylofuranose.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502383c