Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.
Identifieur interne : 000192 ( PubMed/Corpus ); précédent : 000191; suivant : 000193Novel 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 TanakaSource :
- Organic letters [ 1523-7060 ] ; 2004.
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
Links to Exploration step
pubmed:15281734Le 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>
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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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<author><name sortKey="Hashimoto, Kyoko" sort="Hashimoto, Kyoko" uniqKey="Hashimoto K" first="Kyoko" last="Hashimoto">Kyoko Hashimoto</name>
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<author><name sortKey="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</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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<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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<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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