{"title":"D4T的锂化研究。","authors":"H Kumamoto, H Tanaka","doi":"10.1093/nass/44.1.107","DOIUrl":null,"url":null,"abstract":"<p><p>Upon treatment with LTMP, 5'-O-protected D4T undergoes deprotonation of the vinylic proton (H-3' or H-2'): when 5'-O-silyl derivative was used, the 3'-C-silylated product was formed as a result of C3'-lithiation and subsequent O-->C silyl migration, while deprotonation at the 2'-position led to the formation of an allene derivative. A stannyl version of this reaction was also examined to develop a method for C3'-functionalization of D4T.</p>","PeriodicalId":19394,"journal":{"name":"Nucleic acids symposium series","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2000-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/44.1.107","citationCount":"0","resultStr":"{\"title\":\"Lithiation study on D4T.\",\"authors\":\"H Kumamoto, H Tanaka\",\"doi\":\"10.1093/nass/44.1.107\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Upon treatment with LTMP, 5'-O-protected D4T undergoes deprotonation of the vinylic proton (H-3' or H-2'): when 5'-O-silyl derivative was used, the 3'-C-silylated product was formed as a result of C3'-lithiation and subsequent O-->C silyl migration, while deprotonation at the 2'-position led to the formation of an allene derivative. A stannyl version of this reaction was also examined to develop a method for C3'-functionalization of D4T.</p>\",\"PeriodicalId\":19394,\"journal\":{\"name\":\"Nucleic acids symposium series\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2000-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1093/nass/44.1.107\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Nucleic acids symposium series\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1093/nass/44.1.107\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Nucleic acids symposium series","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1093/nass/44.1.107","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Upon treatment with LTMP, 5'-O-protected D4T undergoes deprotonation of the vinylic proton (H-3' or H-2'): when 5'-O-silyl derivative was used, the 3'-C-silylated product was formed as a result of C3'-lithiation and subsequent O-->C silyl migration, while deprotonation at the 2'-position led to the formation of an allene derivative. A stannyl version of this reaction was also examined to develop a method for C3'-functionalization of D4T.
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