{"title":"3′-偶氮基-2′，3′-二脱氧己糖核苷的合成。","authors":"K Walczak, E B Pedersen, C Nielsen","doi":"10.3891/acta.chem.scand.52-0935","DOIUrl":null,"url":null,"abstract":"<p><p>1,8-Diazabicyclo[5.4.0]undec-7-ene salts of 2-methyl-4(5)-nitroimidazole or benzotriazole were obtained in crystalline form. Michael-type addition of these salts to (4S,5R)-(E)-4,6-di-O-acetyl-5-hydroxy-2-hexenal gave, after acetylation of the product, an isomeric mixture of acetylated 3-(azol-1-yl)-2,3-dideoxy-D-arabino-hexopyranosides and 3-(azol-1-yl)-2,3-dideoxy-D-ribo-hexofuranosides. Reaction of these peracetylated adducts with trimethylsilylated thymine in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflate) afforded the corresponding nucleosides which were deprotected by using methanolic ammonia. The nucleosides were found inactive against HIV-1 and HSV-1.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"52 7","pages":"935-41"},"PeriodicalIF":0.0000,"publicationDate":"1998-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"3","resultStr":"{\"title\":\"Synthesis of 3'-azolyl-2',3'-dideoxyhexose nucleosides.\",\"authors\":\"K Walczak, E B Pedersen, C Nielsen\",\"doi\":\"10.3891/acta.chem.scand.52-0935\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>1,8-Diazabicyclo[5.4.0]undec-7-ene salts of 2-methyl-4(5)-nitroimidazole or benzotriazole were obtained in crystalline form. Michael-type addition of these salts to (4S,5R)-(E)-4,6-di-O-acetyl-5-hydroxy-2-hexenal gave, after acetylation of the product, an isomeric mixture of acetylated 3-(azol-1-yl)-2,3-dideoxy-D-arabino-hexopyranosides and 3-(azol-1-yl)-2,3-dideoxy-D-ribo-hexofuranosides. Reaction of these peracetylated adducts with trimethylsilylated thymine in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflate) afforded the corresponding nucleosides which were deprotected by using methanolic ammonia. The nucleosides were found inactive against HIV-1 and HSV-1.</p>\",\"PeriodicalId\":76966,\"journal\":{\"name\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"volume\":\"52 7\",\"pages\":\"935-41\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1998-07-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"3\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.3891/acta.chem.scand.52-0935\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.3891/acta.chem.scand.52-0935","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Synthesis of 3'-azolyl-2',3'-dideoxyhexose nucleosides.
1,8-Diazabicyclo[5.4.0]undec-7-ene salts of 2-methyl-4(5)-nitroimidazole or benzotriazole were obtained in crystalline form. Michael-type addition of these salts to (4S,5R)-(E)-4,6-di-O-acetyl-5-hydroxy-2-hexenal gave, after acetylation of the product, an isomeric mixture of acetylated 3-(azol-1-yl)-2,3-dideoxy-D-arabino-hexopyranosides and 3-(azol-1-yl)-2,3-dideoxy-D-ribo-hexofuranosides. Reaction of these peracetylated adducts with trimethylsilylated thymine in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflate) afforded the corresponding nucleosides which were deprotected by using methanolic ammonia. The nucleosides were found inactive against HIV-1 and HSV-1.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
