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Recent advances in the synthesis of fluorinated nucleosides

Authors:	Xiao-Long Qiu [Author Vitae] [Author Vitae] Feng-Ling Qing [Author Vitae]

Institution:	^a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China ^b College of Chemistry, Chemistry Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China

Abstract:

Keywords:	Ac acetyl AIBN 2 2&prime -azobis(isobutyronitrile) AIDS acquired immune deficiency syndrome Bn benzyl Boc tert-butoxycarbonyl BOM benzyloxymethyl BSA N O-bis(trimethylsilyl)acetamide BSTFA N O-bis(trimethylsilyl)trifluoroacetamide Bz benzoyl CAN ceric ammonium nitrate Cbz benzyloxycarbonyl CMV cytomegalovirus DAST diethylaminosulfur trifluouride DBU 1 8-diazabicyclo[5 4 0]undec-7-ene DCC 1 3-dicyclohexylcarbodiimide DEAD diethyl azodicarboxylate DIAD diisopropyl azodicarboxylate DIBAL-H diisobutylaluminium hydride DIPEA diisopropylethylamine DMAP 4-(dimethylamino)pyridine DMF N N-dimethylformamide DMP 2 2-dimethoxypropane DMS dimethyl sulfide DMSO dimethylsulfoxide DMTr dimethoxytrityl DNA deoxyribonucleic acid DNP 2 4-dinitrophenyl DTBMP 2 6-di-tert-butyl-4-methylpyridine EBV Epstein-Barr virus F-TEDA-BF₄ 1-(chloromethyl)-4-fluoro-1 4-diazabicyclo[2 2 2]-octane bis(tetrafluoroborate) HBV hepatitis B virus HCV hepatitis C virus HIV human immunodeficiency virus HMDS hexamethyldisilazane HMPA hexamethylphosphoramide HMPT hexamethylphosphorous triamide HSV herpes simplex virus HWE Horner-Wadsworth-Emmons LDA lithium diisopropylamide LiHMDS lithium bis(trimethylsilyl)amide LTMP lithium tetramethylpiperidide m-CPBA meta-chloroperbenzoic acid MEM methoxyethoxymethyl MMT (MMTr) p-methoxyphenyldiphenylmethyl Ms methanesulfonyl NaHMDS sodium bis(trimethylsilyl)amide NBA N-bromoacetamide NBS N-bromosuccinimide NCS N-chlorosuccinimide NfF perfluorobutanesulfonyl fluoride NFSI N-fluorobenzenesulfonimide NMO (NMMO) N-methylmorpholine N-oxide N-PSP N-(phenylseleno)phthalimide RCM ring-closing metathesis p-An p-methoxyphenyl PCC pyridinium chlorochromate PDC pyridinium dichromate Piv pivaloyl PMB p-methoxybenzyl p-TSA p-toluenesulfonic acid Py pyridine RNA ribonucleic acid SAR structure-activity relationship SEM trimethylsilylethoxymethyl TASF tris(dimethylamino)sulfur (trimethylsilyl)difluoride TBAF tetrabutylammonium fluoride TBAI tetrabutylammonium iodide TBDMS (TBS) tert-butyldimethylsilyl TBDPS tert-butyldiphenylsilyl TCDI 1 1&prime -thiocarbonyldiimidazole TEA triethylamine TEMPO 2 2 6 6-tetramethylpiperidinyloxy TEPA triethyl phosphonoacetate Tf trifluoromethanesulfonyl TFA trifluoroacetic acid TFAA trifluoroacetic acid anhydride THF tetrahydrofuran THP tetrahydropyranyl TIPDS (TPDS) 1 3-(1 1 3 3-tetraisopropyldisiloxanylidene) TMP 2 2 6 6-tetramethylpiperidine TMS trimethylsilyl TMSOTf trimethylsilyl triflate Tol toluoyl TPP triphenylphosphine Tr triphenylmethyl (trityl) Ts p-toluenesulfonyl (tosyl) VZV varicella zoster virus
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