Full metadata record
DC Field | Value | Language |
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dc.contributor.author | 정낙신 | - |
dc.date.accessioned | 2016-08-28T11:08:12Z | - |
dc.date.available | 2016-08-28T11:08:12Z | - |
dc.date.issued | 2009 | - |
dc.identifier.issn | 1001-604X | - |
dc.identifier.other | OAK-13384 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/229389 | - |
dc.description.abstract | Synthesis of north-5'-methylbicyclo[3.1.0]hexyl purine and pyrimidine nucleosides with an ethynyl group at C-3' position has been successfully accomplished by a facile method. Methylbicyclo[3.1.0]hexanone (±)-5 having three contiguous chiral centers was remarkably simply constructed only by four steps containing a carbenoid insertion reaction in the presence of rhodium(II) acetate dimer and CuSO 4, giving a correct relative stereochemistry of the generated three chiral centers. Upon Grignard reaction of (±)-5 with ethynylmagnesium bromide, exclusive diastereoselectivity was observed. Condensation of glycosyl donor (±)-9 with purine nucleobase afforded only the desired N9-alkylated nucleoside, while condensation with pyrimidine, N 3-benzoylated uracil gave the desired N1-alkylated nucleoside (±)-13 with the undesired O 2-alkylated nucleoside (±)-14. Probably, (±)-14 would be formed due to steric hindrance caused upon approaching for N1-alkylation. © 2009 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | - |
dc.language | English | - |
dc.title | Highly concise synthesis of 3'-"up"-ethynyl-5'-methylbicyclo- [3.1.0]hexyl purine and pyrimidine nucleoside derivatives using rhodium(II) carbenoid cycloaddition and highly diastereoselective Grignard reaction | - |
dc.type | Article | - |
dc.relation.issue | 12 | - |
dc.relation.volume | 27 | - |
dc.relation.index | SCI | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.startpage | 2405 | - |
dc.relation.lastpage | 2412 | - |
dc.relation.journaltitle | Chinese Journal of Chemistry | - |
dc.identifier.doi | 10.1002/cjoc.201090016 | - |
dc.identifier.wosid | WOS:000273627600017 | - |
dc.identifier.scopusid | 2-s2.0-77749326697 | - |
dc.author.google | Yang Z. | - |
dc.author.google | Kim K.R. | - |
dc.author.google | Park A.-Y. | - |
dc.author.google | Lee H.-R. | - |
dc.author.google | Kang J.-A. | - |
dc.author.google | Kim W.H. | - |
dc.author.google | Chun P. | - |
dc.author.google | Gong P. | - |
dc.author.google | Lee B. | - |
dc.author.google | Jeong L.S. | - |
dc.author.google | Moon H.R. | - |
dc.contributor.scopusid | 정낙신(16028528200) | - |
dc.date.modifydate | 20211210153610 | - |