Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.
Identifieur interne : 001549 ( Main/Exploration ); précédent : 001548; suivant : 001550Novel 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
Affiliations:
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Le document en format XML
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Shiina</name></author><author><name sortKey="Yoshimura, Yuichi" sort="Yoshimura, Yuichi" uniqKey="Yoshimura Y" first="Yuichi" last="Yoshimura">Yuichi Yoshimura</name></author><author><name sortKey="Shimada, Hisashi" sort="Shimada, Hisashi" uniqKey="Shimada H" first="Hisashi" last="Shimada">Hisashi Shimada</name></author><author><name sortKey="Hashimoto, Kyoko" sort="Hashimoto, Kyoko" uniqKey="Hashimoto K" first="Kyoko" last="Hashimoto">Kyoko Hashimoto</name></author><author><name sortKey="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2004">2004</date><idno type="RBID">pubmed:15281734</idno><idno type="pmid">15281734</idno><idno type="doi">10.1021/ol040035u</idno><idno type="wicri:Area/PubMed/Corpus">000192</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000192</idno><idno 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last="Haraguchi">Kazuhiro Haraguchi</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. harakazu@pharm.showa-u.ac.jp</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Shiina, Noriaki" sort="Shiina, Noriaki" uniqKey="Shiina N" first="Noriaki" last="Shiina">Noriaki Shiina</name></author><author><name sortKey="Yoshimura, Yuichi" sort="Yoshimura, Yuichi" uniqKey="Yoshimura Y" first="Yuichi" last="Yoshimura">Yuichi Yoshimura</name></author><author><name sortKey="Shimada, Hisashi" sort="Shimada, Hisashi" uniqKey="Shimada H" first="Hisashi" last="Shimada">Hisashi Shimada</name></author><author><name sortKey="Hashimoto, Kyoko" sort="Hashimoto, Kyoko" uniqKey="Hashimoto K" first="Kyoko" last="Hashimoto">Kyoko Hashimoto</name></author><author><name sortKey="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</name></author></analytic><series><title level="j">Organic letters</title><idno type="ISSN">1523-7060</idno><imprint><date when="2004" type="published">2004</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Molecular Structure</term><term>Siloxanes (chemistry)</term><term>Stereoisomerism</term><term>Thionucleosides (chemical synthesis)</term><term>Thiophenes (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Siloxanes ()</term><term>Structure moléculaire</term><term>Stéréoisomérie</term><term>Thionucléosides (synthèse chimique)</term><term>Thiophènes ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Thionucleosides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Siloxanes</term><term>Thiophenes</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Thionucléosides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Siloxanes</term><term>Structure moléculaire</term><term>Stéréoisomérie</term><term>Thiophènes</term></keywords></textClass></profileDesc></teiHeader><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></front></TEI><affiliations><list><country><li>Japon</li></country><region><li>Région de Kantō</li></region><settlement><li>Tokyo</li></settlement></list><tree><noCountry><name sortKey="Hashimoto, Kyoko" sort="Hashimoto, Kyoko" uniqKey="Hashimoto K" first="Kyoko" last="Hashimoto">Kyoko Hashimoto</name><name sortKey="Shiina, Noriaki" sort="Shiina, Noriaki" uniqKey="Shiina N" first="Noriaki" last="Shiina">Noriaki Shiina</name><name sortKey="Shimada, Hisashi" sort="Shimada, Hisashi" uniqKey="Shimada H" first="Hisashi" last="Shimada">Hisashi Shimada</name><name sortKey="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</name><name sortKey="Yoshimura, Yuichi" sort="Yoshimura, Yuichi" uniqKey="Yoshimura Y" first="Yuichi" last="Yoshimura">Yuichi Yoshimura</name></noCountry><country name="Japon"><region name="Région de Kantō"><name sortKey="Haraguchi, Kazuhiro" sort="Haraguchi, Kazuhiro" uniqKey="Haraguchi K" first="Kazuhiro" last="Haraguchi">Kazuhiro Haraguchi</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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