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Synthesis of N 6 , N 6 ‐Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ
Reactions between secondary amines and phosphorus trichloride (PCl 3 ) leads to the formation of the corresponding tris(dialkylamino)phosphanes or hexaalkylphosphorus triamides [HAPTs: (R 2 N) 3 P]. Treatment of silyl‐protected 2′‐deoxyinosine and acetyl‐protected inosine with the HAPTs produced in...
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| Published in: | European journal of organic chemistry 2009-01, Vol.2009 (1), p.152-159 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c169t-f442db490e13e92c1506940bc7b17e49b9fccaf665d8f1a8dbedb05e5d964c383 |
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| cites | cdi_FETCH-LOGICAL-c169t-f442db490e13e92c1506940bc7b17e49b9fccaf665d8f1a8dbedb05e5d964c383 |
| container_end_page | 159 |
| container_issue | 1 |
| container_start_page | 152 |
| container_title | European journal of organic chemistry |
| container_volume | 2009 |
| creator | Lakshman, Mahesh K. Choudhury, Asad Bae, Suyeal Rochttis, Eliezer Pradhan, Padmanava Kumar, Amit |
| description | Reactions between secondary amines and phosphorus trichloride (PCl
3
) leads to the formation of the corresponding tris(dialkylamino)phosphanes or hexaalkylphosphorus triamides [HAPTs: (R
2
N)
3
P]. Treatment of silyl‐protected 2′‐deoxyinosine and acetyl‐protected inosine with the HAPTs produced in situ, together with iodine (I
2
), leads to the formation of
N
6
,
N
6
‐dialkyladenosine and ‐2′‐deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I
2
has been studied by
31
P{
1
H} NMR spectroscopy.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) |
| doi_str_mv | 10.1002/ejoc.200800752 |
| format | article |
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3
) leads to the formation of the corresponding tris(dialkylamino)phosphanes or hexaalkylphosphorus triamides [HAPTs: (R
2
N)
3
P]. Treatment of silyl‐protected 2′‐deoxyinosine and acetyl‐protected inosine with the HAPTs produced in situ, together with iodine (I
2
), leads to the formation of
N
6
,
N
6
‐dialkyladenosine and ‐2′‐deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I
2
has been studied by
31
P{
1
H} NMR spectroscopy.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200800752</identifier><language>eng</language><ispartof>European journal of organic chemistry, 2009-01, Vol.2009 (1), p.152-159</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c169t-f442db490e13e92c1506940bc7b17e49b9fccaf665d8f1a8dbedb05e5d964c383</citedby><cites>FETCH-LOGICAL-c169t-f442db490e13e92c1506940bc7b17e49b9fccaf665d8f1a8dbedb05e5d964c383</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Lakshman, Mahesh K.</creatorcontrib><creatorcontrib>Choudhury, Asad</creatorcontrib><creatorcontrib>Bae, Suyeal</creatorcontrib><creatorcontrib>Rochttis, Eliezer</creatorcontrib><creatorcontrib>Pradhan, Padmanava</creatorcontrib><creatorcontrib>Kumar, Amit</creatorcontrib><title>Synthesis of N 6 , N 6 ‐Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ</title><title>European journal of organic chemistry</title><description>Reactions between secondary amines and phosphorus trichloride (PCl
3
) leads to the formation of the corresponding tris(dialkylamino)phosphanes or hexaalkylphosphorus triamides [HAPTs: (R
2
N)
3
P]. Treatment of silyl‐protected 2′‐deoxyinosine and acetyl‐protected inosine with the HAPTs produced in situ, together with iodine (I
2
), leads to the formation of
N
6
,
N
6
‐dialkyladenosine and ‐2′‐deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I
2
has been studied by
31
P{
1
H} NMR spectroscopy.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</description><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNo9kEFOwzAQRS0EEqWwZe0DkDJOHCdeogItUlWQ2krsIsceU5c0qexGIjuOwBk5CWlBLP78WTyNNI-QawYjBhDf4qbRoxggB8jS-IQMGEgZgZBw2u884RGTyes5uQhhAwBSCDYgbtHV-zUGF2hj6ZwKenOc359f905V712lDNauRjpvdYVNcAYDXQVXv9Epfqgjsls3oY9vA116p7ZH5sU3ptVoqKvpwu3bS3JmVRXw6q-HZPX4sBxPo9nz5Gl8N4s0E3IfWc5jU3IJyBKUsWZp_wGHUmcly5DLUlqtlRUiNbllKjclmhJSTI0UXCd5MiSj37vaNyF4tMXOu63yXcGgOIgqDqKKf1HJD6BxXlw</recordid><startdate>200901</startdate><enddate>200901</enddate><creator>Lakshman, Mahesh K.</creator><creator>Choudhury, Asad</creator><creator>Bae, Suyeal</creator><creator>Rochttis, Eliezer</creator><creator>Pradhan, Padmanava</creator><creator>Kumar, Amit</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200901</creationdate><title>Synthesis of N 6 , N 6 ‐Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ</title><author>Lakshman, Mahesh K. ; Choudhury, Asad ; Bae, Suyeal ; Rochttis, Eliezer ; Pradhan, Padmanava ; Kumar, Amit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c169t-f442db490e13e92c1506940bc7b17e49b9fccaf665d8f1a8dbedb05e5d964c383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lakshman, Mahesh K.</creatorcontrib><creatorcontrib>Choudhury, Asad</creatorcontrib><creatorcontrib>Bae, Suyeal</creatorcontrib><creatorcontrib>Rochttis, Eliezer</creatorcontrib><creatorcontrib>Pradhan, Padmanava</creatorcontrib><creatorcontrib>Kumar, Amit</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lakshman, Mahesh K.</au><au>Choudhury, Asad</au><au>Bae, Suyeal</au><au>Rochttis, Eliezer</au><au>Pradhan, Padmanava</au><au>Kumar, Amit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of N 6 , N 6 ‐Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ</atitle><jtitle>European journal of organic chemistry</jtitle><date>2009-01</date><risdate>2009</risdate><volume>2009</volume><issue>1</issue><spage>152</spage><epage>159</epage><pages>152-159</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Reactions between secondary amines and phosphorus trichloride (PCl
3
) leads to the formation of the corresponding tris(dialkylamino)phosphanes or hexaalkylphosphorus triamides [HAPTs: (R
2
N)
3
P]. Treatment of silyl‐protected 2′‐deoxyinosine and acetyl‐protected inosine with the HAPTs produced in situ, together with iodine (I
2
), leads to the formation of
N
6
,
N
6
‐dialkyladenosine and ‐2′‐deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I
2
has been studied by
31
P{
1
H} NMR spectroscopy.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</abstract><doi>10.1002/ejoc.200800752</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 1434-193X |
| ispartof | European journal of organic chemistry, 2009-01, Vol.2009 (1), p.152-159 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley:Jisc Collections:Wiley Read and Publish Open Access 2024-2025 (reading list) |
| title | Synthesis of N 6 , N 6 ‐Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ |
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