Source:http://linkedlifedata.com/resource/pubmed/id/16808515
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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
14
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pubmed:dateCreated |
2006-6-30
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pubmed:abstractText |
CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl- and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz-protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Copper,
http://linkedlifedata.com/resource/pubmed/chemical/Ethers,
http://linkedlifedata.com/resource/pubmed/chemical/Hydrocarbons, Iodinated,
http://linkedlifedata.com/resource/pubmed/chemical/Iodides,
http://linkedlifedata.com/resource/pubmed/chemical/Sarcosine,
http://linkedlifedata.com/resource/pubmed/chemical/Tyrosine,
http://linkedlifedata.com/resource/pubmed/chemical/cuprous iodide,
http://linkedlifedata.com/resource/pubmed/chemical/dimethylglycine
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pubmed:status |
MEDLINE
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pubmed:month |
Jul
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pubmed:issn |
0022-3263
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
7
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pubmed:volume |
71
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
5268-73
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pubmed:meshHeading |
pubmed-meshheading:16808515-Catalysis,
pubmed-meshheading:16808515-Copper,
pubmed-meshheading:16808515-Ethers,
pubmed-meshheading:16808515-Hydrocarbons, Iodinated,
pubmed-meshheading:16808515-Iodides,
pubmed-meshheading:16808515-Molecular Structure,
pubmed-meshheading:16808515-Sarcosine,
pubmed-meshheading:16808515-Stereoisomerism,
pubmed-meshheading:16808515-Tyrosine
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pubmed:year |
2006
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pubmed:articleTitle |
Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives.
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pubmed:affiliation |
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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