LrgpV1, PubMed, Corpus, bibRecord, 000192

Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.

Identifieur interne : 000192 ( PubMed/Corpus ); précédent : 000191; suivant : 000193

Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.

Auteurs : Kazuhiro Haraguchi ; Noriaki Shiina ; Yuichi Yoshimura ; Hisashi Shimada ; Kyoko Hashimoto ; Hiromichi Tanaka

Source :

Organic letters [ 1523-7060 ] ; 2004.

RBID : pubmed:15281734

English descriptors

KwdEn :
- Molecular Structure, Siloxanes (chemistry), Stereoisomerism, Thionucleosides (chemical synthesis), Thiophenes (chemistry).
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

Links to Exploration step

pubmed:15281734

Le document en format XML

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<author><name sortKey="Haraguchi, Kazuhiro" sort="Haraguchi, Kazuhiro" uniqKey="Haraguchi K" first="Kazuhiro" last="Haraguchi">Kazuhiro Haraguchi</name>
<affiliation><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>
</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>
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<sourceDesc><biblStruct><analytic><title xml:lang="en">Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.</title>
<author><name sortKey="Haraguchi, Kazuhiro" sort="Haraguchi, Kazuhiro" uniqKey="Haraguchi K" first="Kazuhiro" last="Haraguchi">Kazuhiro Haraguchi</name>
<affiliation><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>
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<author><name sortKey="Shiina, Noriaki" sort="Shiina, Noriaki" uniqKey="Shiina N" first="Noriaki" last="Shiina">Noriaki Shiina</name>
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<author><name sortKey="Yoshimura, Yuichi" sort="Yoshimura, Yuichi" uniqKey="Yoshimura Y" first="Yuichi" last="Yoshimura">Yuichi Yoshimura</name>
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<author><name sortKey="Shimada, Hisashi" sort="Shimada, Hisashi" uniqKey="Shimada H" first="Hisashi" last="Shimada">Hisashi Shimada</name>
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<series><title level="j">Organic letters</title>
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<term>Siloxanes (chemistry)</term>
<term>Stereoisomerism</term>
<term>Thionucleosides (chemical synthesis)</term>
<term>Thiophenes (chemistry)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Thionucleosides</term>
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<keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</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>
</front>
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<Month>07</Month>
<Day>29</Day>
</DateCreated>
<DateCompleted><Year>2005</Year>
<Month>03</Month>
<Day>02</Day>
</DateCompleted>
<DateRevised><Year>2006</Year>
<Month>11</Month>
<Day>15</Day>
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<Month>Aug</Month>
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<Title>Organic letters</Title>
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<ArticleTitle>Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.</ArticleTitle>
<Pagination><MedlinePgn>2645-8</MedlinePgn>
</Pagination>
<Abstract><AbstractText>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]</AbstractText>
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Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.

Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.

Source :

English descriptors

Abstract

Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

Pour générer des pages wiki