Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.
Identifieur interne : 000059 ( Ncbi/Curation ); précédent : 000058; suivant : 000060Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.
Auteurs : Kazuhiro Haraguchi [Japon] ; Noriaki Shiina ; Yuichi Yoshimura ; Hisashi Shimada ; Kyoko Hashimoto ; Hiromichi TanakaSource :
- Organic letters [ 1523-7060 ] ; 2004.
Descripteurs français
- KwdFr :
- MESH :
- synthèse chimique : Thionucléosides.
- Siloxanes, Structure moléculaire, Stéréoisomérie, Thiophènes.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Thionucleosides.
- chemical , chemistry : Siloxanes, Thiophenes.
- Molecular Structure, Stereoisomerism.
Abstract
2'-Beta-methyl- and 2'-beta-hydroxymethyl-2'-deoxy-4'-thionucleosides have been synthesized through PhSeCl-mediated electrophilic glycosidation using 4-thiofuranoid glycals having carbon substituents at the C2-position as a glycosyl donor. Preparation of these glycals were carried out by means of the C2 lithiation of 1-chloro-4-thiofuranoid glycal with LTMP followed by the Birch reduction of the chlorine atom. [reaction: see text]
DOI: 10.1021/ol040035u
PubMed: 15281734
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pubmed:15281734Le document en format XML
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<term>Stereoisomerism</term>
<term>Thionucleosides (chemical synthesis)</term>
<term>Thiophenes (chemistry)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Siloxanes ()</term>
<term>Structure moléculaire</term>
<term>Stéréoisomérie</term>
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<front><div type="abstract" xml:lang="en">2'-Beta-methyl- and 2'-beta-hydroxymethyl-2'-deoxy-4'-thionucleosides have been synthesized through PhSeCl-mediated electrophilic glycosidation using 4-thiofuranoid glycals having carbon substituents at the C2-position as a glycosyl donor. Preparation of these glycals were carried out by means of the C2 lithiation of 1-chloro-4-thiofuranoid glycal with LTMP followed by the Birch reduction of the chlorine atom. [reaction: see text]</div>
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