Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.
Identifieur interne : 001717 ( Main/Exploration ); précédent : 001716; suivant : 001718Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.
Auteurs : Hiroki Kumamoto [Japon] ; Hiromichi TanakaSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2002.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Stavudine.
- synthèse chimique : Agents antiVIH, Stavudine.
- Anions, Composés vinyliques, Lithium.
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
Affiliations:
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Le document en format XML
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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></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="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</name></noCountry><country name="Japon"><region name="Région de Kantō"><name sortKey="Kumamoto, Hiroki" sort="Kumamoto, Hiroki" uniqKey="Kumamoto H" first="Hiroki" last="Kumamoto">Hiroki Kumamoto</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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