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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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><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">12027663</PMID><DateCreated><Year>2002</Year><Month>05</Month><Day>24</Day></DateCreated><DateCompleted><Year>2002</Year><Month>11</Month><Day>19</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0022-3263</ISSN><JournalIssue CitedMedium="Print"><Volume>67</Volume><Issue>11</Issue><PubDate><Year>2002</Year><Month>May</Month><Day>31</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.</ArticleTitle><Pagination><MedlinePgn>3541-7</MedlinePgn></Pagination><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></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kumamoto</LastName><ForeName>Hiroki</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. hirotnk@pharm.showa-u.ac.jp</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Tanaka</LastName><ForeName>Hiromichi</ForeName><Initials>H</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000838">Anions</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D019380">Anti-HIV Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014753">Vinyl Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>9FN79X2M3F</RegistryNumber><NameOfSubstance UI="D008094">Lithium</NameOfSubstance></Chemical><Chemical><RegistryNumber>BO9LE4QFZF</RegistryNumber><NameOfSubstance UI="D018119">Stavudine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N" UI="D000838">Anions</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D019380">Anti-HIV Agents</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000138">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D008094">Lithium</DescriptorName><QualifierName MajorTopicYN="N" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D018119">Stavudine</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000031">analogs & derivatives</QualifierName><QualifierName MajorTopicYN="N" UI="Q000138">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D014753">Vinyl Compounds</DescriptorName><QualifierName MajorTopicYN="N" UI="Q000737">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2002</Year><Month>5</Month><Day>25</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2002</Year><Month>11</Month><Day>26</Day><Hour>4</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2002</Year><Month>5</Month><Day>25</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">12027663</ArticleId><ArticleId IdType="pii">jo0107958</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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