Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.
Identifieur interne : 000215 ( PubMed/Corpus ); précédent : 000214; suivant : 000216Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.
Auteurs : Hiroki Kumamoto ; Hiromichi TanakaSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2002.
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Stavudine.
- chemical , chemical synthesis : Anti-HIV Agents, Stavudine.
- chemical , chemistry : Lithium, Vinyl Compounds.
- chemical : Anions.
Abstract
Reaction of 5'-O-protected derivatives of the anti-HIV agent stavudine (d4T) with LTMP was investigated with the aim to lithiate the vinylic hydrogens (H-3' and H-2'). When the lithiation of the 5'-O-tert-butyldiphenylsilyl derivative 5 was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3'-C-silylated product 4a. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogues variously substituted at the 3'-position by manipulating the 3'-C-stannyl d4T as a common intermediate.
PubMed: 12027663
Links to Exploration step
pubmed:12027663Le document en format XML
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<author><name sortKey="Kumamoto, Hiroki" sort="Kumamoto, Hiroki" uniqKey="Kumamoto H" first="Hiroki" last="Kumamoto">Hiroki Kumamoto</name>
<affiliation><nlm:affiliation>School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. hirotnk@pharm.showa-u.ac.jp</nlm:affiliation>
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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="Kumamoto, Hiroki" sort="Kumamoto, Hiroki" uniqKey="Kumamoto H" first="Hiroki" last="Kumamoto">Hiroki Kumamoto</name>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anions</term>
<term>Anti-HIV Agents (chemical synthesis)</term>
<term>Lithium (chemistry)</term>
<term>Stavudine (analogs & derivatives)</term>
<term>Stavudine (chemical synthesis)</term>
<term>Vinyl Compounds (chemistry)</term>
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<keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Stavudine</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Stavudine</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Lithium</term>
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<front><div type="abstract" xml:lang="en">Reaction of 5'-O-protected derivatives of the anti-HIV agent stavudine (d4T) with LTMP was investigated with the aim to lithiate the vinylic hydrogens (H-3' and H-2'). When the lithiation of the 5'-O-tert-butyldiphenylsilyl derivative 5 was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3'-C-silylated product 4a. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogues variously substituted at the 3'-position by manipulating the 3'-C-stannyl d4T as a common intermediate.</div>
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<Title>The Journal of organic chemistry</Title>
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<ArticleTitle>Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.</ArticleTitle>
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<Abstract><AbstractText>Reaction of 5'-O-protected derivatives of the anti-HIV agent stavudine (d4T) with LTMP was investigated with the aim to lithiate the vinylic hydrogens (H-3' and H-2'). When the lithiation of the 5'-O-tert-butyldiphenylsilyl derivative 5 was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3'-C-silylated product 4a. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogues variously substituted at the 3'-position by manipulating the 3'-C-stannyl d4T as a common intermediate.</AbstractText>
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