CAS: 784-71-4; 1-((2R,3R,4R,5R)-3-Fluoro-4-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)Pyrimidine-2,4(1H,3H)-Dione

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69123-94-0 114248-23-6 163252-36-6

欧盟法规

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上下游产品

uracil9-2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyluracil 1-(3',5'-di-O-trityl-β-D-arabinofuranosyl)uracil 5',3'-bis-O-trityl-2'-fluoro-2'-deoxyuridine 2,2'-Anhydrouridine 5'-O-trityl-2'-deoxy-2'-fluorouridine 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 2'-fluorodeoxyadenosine 2'-Deoxy-2,2'-difluoro-adenosine

在 甲醇,2,3-二氯-5,6-二氰基-1,4-苯醌体系中,化学反应 0.67H,以91%的收率获得产物2'-氟-2'-脱氧尿苷
参考文献:Ddq介导的伯醇区域特异性保护和中性条件下的脱保护:新型对甲氧基苄基-Pixyl醚作为核苷保护选择试剂的应用
标题:Ddq介导的伯醇区域特异性保护和中性条件下的脱保护:新型对甲氧基苄基-Pixyl醚作为核苷保护选择试剂的应用
摘要:一个简单的,高效的协议被用于在两个核苷和其它分子与伯羟基的保护regiosepecific描述p-米乙氧基b Enzyl 2,7-D Imethyl P Ixyl ë疗法(mbdpe)中的存在2,3-二氯5,6-二氰基-1,4-苯醌(ddq).此外,用ddq在meoh中快速脱保护2,7-二甲基pixyl(dmpx).两种方法均在革兰氏级合成修饰核苷上成功实现.该方案为dmpx基团的选择性保护和脱保护提供了温和和中性的条件,同时可与其他常规保护基团(例如苯甲酰基,苄基,Thp,Tbdps和丙酮化物)相容.
DOI:10.1016/j.Tetlet.2017.05.066

专利信息

专利号:US-9884885-B2
优先权日:2009-05-18
标题:Synthesis of labile base protected-modified deoxy and modified ribo nucleosides, corresponding phosphoramidites and supports and their use in high purity oligonucleotide synthesis
发明人：SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
摘要:This invention relates to novel method of synthesis of RNA utilizing N-2-acetyl protected guanine as nucleoside base, nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-acetyl protected guanine as nucleoside base protecting group, which is significantly faster base labile protecting group, yet significantly more stable than commonly utilized-2-isobutyryl guanosine is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups, including acetyl group from guanine and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of acetyl protecting groups of the natural deoxy and ribonucleosides occurs under substantially reduced time in contact with mild deprotection conditions such as mild bases, secondary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is designed to lead to high purity large scale therapeutic grade oligonucleotide chimeras which consist of fluoro sugar modification in conjunction with deoxy nucleosides, ribonucleosides, modified base and modified sugar nucleosides. This approach is further designed to use acetyl guanine protecting group when other bases are sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides.

专利号:US-8981076-B2
优先权日:2008-11-29
标 题 :Synthesis of N-FMOC protected deoxy nucleosides, ribo nucleosides, modified deoxy and ribo nucleosides, and phosphoramidites, and their use in oligonucleotide synthesis
发明人：SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
摘要:This invention relates to synthesis of novel -N-FMOC protected nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-FMOC as nucleoside base protecting group, which is highly base labile protecting group is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of FMOC protecting groups of the natural deoxy and ribonucleosides occurs under very mild deprotection conditions such as mild bases, secondary and tertiary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is further designed to use FMOC protecting group on various base sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides. DNA oligonucleotides containing 3′-end dA at the 3′-terminal will be produced using the FMOC-dA-supports would lead to much reduced M−1 deletion sequences, and thereby high purity.

专利号:US-11858953-B2
优先权日:2018-04-04
标 题:Compositions and methods for synthesis of phosphorylated molecules
发明人：CHAPUT JOHN; LIAO JEN-YU; BALA SAIKAT
权利人:UNIV CALIFORNIA
摘要:The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

专利号:US-6624294-B2
优先权日:1999-01-08
标 题:Regioselective synthesis of 2′-O-modified nucleosides
发明人：KAWASAKI ANDREW M; FRASER ALLISTER S; MANOHARAN MUTHIAH; COOK P DAN; PRAKASH THAZHA P
权利人:ISIS PHARMACEUTICALS INC
摘要:Methods for the regioselective alkylation at the 2'-hydroxy position over the 3'-hydroxy position of nucleosides and nucleoside analogs, forming 2'-O-ester modified compounds, are disclosed. Reduction and derivatization of the 2'-O-ester provides 2'-O-modified nucleosides and nucleoside analogs useful for the synthesis of oligomeric compounds having improved hybridization affinity and nuclease resistance.

专利号:US-2025197439-A1
优先权日:2022-03-18
标 题:Decarboxylative acetoxylation using mn(ii) or mn(iii) reagent for synthesis of 4'-acetoxy-nucleoside and use thereof for synthesis of corresponding 4'-(dimethoxyphosphoryl)methoxy-nucleotide
发明人：VAGLE KURT EDRIC; BHADURI SAYANTAN; YANG GUOHAN
权利人:DICERNA PHARMACEUTICALS INC
摘要:The present invention relates to the preparation of nucleic acids, nucleosides, nucleotides, and analogues thereof useful as potent and stable RNA interference agents. The present invention provides improved yields and avoids the use of lead tetraacetate for decarboxylative acetylation which decreases the overall cost of production by removing the need for lead remediation and offers a significant reduction in the environmental costs in production.

专利号:US-8912319-B2
优先权日:2010-07-15
标 题 :Synthesis of 2′-deoxy-2′-[18F]fluoro-5-methyl-1-B-D-arabinofuranosyluracil (18F-FMAU)
发明人：LI ZIBO; CAI HANCHENG; CONTI PETER S
权利人:LI ZIBO; CAI HANCHENG; CONTI PETER S; UNIV SOUTHERN CALIFORNIA
摘要:The present invention relates to methods of synthesizing 18 F-FMAU. In particular, 18 F-FMAU is synthesized using one-pot reaction conditions in the presence of Friedel-Crafts catalysts. The one-pot reaction conditions are incorporated into a fully automated cGMP-compliant radiosynthesis module, which results in a reduction in synthesis time and simplifies reaction conditions. The one-pot reaction conditions are also suitable for the production of 5-substituted thymidine or cytidine analogs. The products from the one-pot reaction (e.g. the labeled thymidine or cytidine analogs) can be used as probes for imaging tumor proliferative activity. More specifically, these [ 18 F]-labeled thymidine or cytidine analogs can be used as a PET tracer for certain medical conditions, including, but not limited to, cancer disease, autoimmunity inflammation, and bone marrow transplant.