CAS: 961-07-9; 2-Amino-9-((2R,4S,5R)-4-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)-3,9-Dihydro-6H-Purin-6-One

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鸟苷置于吡啶,咪唑,Ammonium Hydroxide,偶氮二异丁腈,四丁基氟化铵,三正丁基氢锡,溶剂黄146体系中,用 四氢呋喃,甲醇,N,N-二甲基甲酰胺,甲苯 作为反应溶剂,化学反应 149.0H,反应生成 2'-脱氧鸟苷
参考文献:Preparation Of 2'-O-(.Beta.-Cyanoethyl Phosphoramidites) Of 3'-Deoxycytidine And 3'-Deoxyguanosine And Their Use For Solid-Phase Synthesis Of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages
标题:Preparation Of 2'-O-(.Beta.-Cyanoethyl Phosphoramidites) Of 3'-Deoxycytidine And 3'-Deoxyguanosine And Their Use For Solid-Phase Synthesis Of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages
摘要:Convenient,Preparative Scale Synthetic Routes To 2'-O-(Beta-Cyanoethyl N,N-Diisopropylphosphoramidites) Of 3'-Deoxycytidine (1) And 3'-Deoxyguanosine (2) Are Described. The 3'-Deoxycytidine Nucleoside 5 Was Constructed By A Modified Hilbert-Johnson Reaction In Which N-(4-Isobutyryl)-Cytosine (4) Was Ribosylated With Anomeric Acetate 3. Nucleoside 5 Was Converted To 5'-O(Dimethoxytrityl)-4-N-Isobutyryl-3'-Deoxycytidine (7) And Phosphitylated To Provide Phosphoramidite 1. Access To Derivatives Of 3'-Deoxyguanosine Was Provided By Selective Removal Of The 3'-Hydroxyl Of Guanosine (10). Thus,The 3'-O-Thiocarbamate Of 5'-O-(Dimethoxytrityl)-2-N-(Dimethylformamidyl)-2'-O-(Triisopropylsilyl)Guanosine (12) Was Reduced With Tributyltin Hydride And Converted To Phosphoramidite 2. In Results To Be Reported Elsewhere,Phosphoramidites 1 And 2 Were Used To Prepare Oligodeoxynucleotides Containing Novel 2',5'-Phosphodiester Linkages Using Automated Solid-Phase Dna Synthesis Methods With Average Stepwise Coupling Yields Of >97%.
DOI:10.1021/jo00103A014

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-8193384-B2
优先权日:2005-07-29
标 题 :Polymer-bound phosphitylating reagents for the synthesis of organophosphorus compounds
发明人：PARANG KEYKAVOUS; AHAMDIBENI YOUSEF
权利人:PARANG KEYKAVOUS; AHAMDIBENI YOUSEF; RHODE ISLAND EDUCATION
摘要:The synthesis and biochemical utility of modified oligonucleotides containing diphosphodiester internucleotide linkages. The synthesis of these compounds was carried out using diphosphitylating reagents. Oligonucleotides containing diphosphate diester bridges wherein said oligonucleotides are synthesized via a solid-phase synthesis strategy to form modified oligonucleotides. Diphosphitylating, triphosphitylating, tetraphosphitylating, β-triphosphitylating, bifunctional diphosphitylating, bifunctional triphosphitylating, and bifunctional tetraphosphitylating reagents wherein, the phosphorus atoms are linked together through oxygen, sulfur, amino, or methylene groups and/or are substituted with chlorine, diisopropylamine and cyanoethoxy groups.

专利号:US-5623068-A
优先权日:1994-03-07
标 题:Synthesis of DNA using substituted phenylacetyl-protected nucleotides
发明人：REDDY M PARAMESWARA; FAROOQUI FIRDOUS; HANNA NAEEM B
权利人:BECKMAN INSTRUMENTS INC
摘要:Deoxyribonucleotide and ribonucleotide derivatives of the general formula I I wherein R1 represents -CR'R''-Ar, in which Ar is substituted aryl (as hereinafter defined) and R' and R'' are independently selected from the group consisting of hydrogen and lower alkyl; one of -R2 and R3 is a hydroxyl-protecting group and the other is a group suitable for synthesis of polynucleotides or for attachment of the nucleotide to a solid support; R4 is selected from the group consisting of hydrogen, -OH and protected hydroxyl; and B represents a divalent radical corresponding to a purine or pyrimidine base. When synthesis is carried out using these derivatives, the deprotection procedure is reduced to an essentially instantaneous process. The derivatives have acceptable shelf life and are very stable to conventional DNA synthesis conditions. Particularly preferred are those compounds wherein Ar is mono- and dihalo-substituted phenyl.

专利号:US-5204456-A
优先权日:1986-04-08
标题:Derivatives of nucleosides and their use for the synthesis of oligonucleotides
发明人：MOLKO DIDIER; SCHULHOF JEAN-CLAUDE; TEOULE ROBERT
权利人:COMMISSARIAT ENERGIE ATOMIQUE
摘要:The invention relates to derivatives of nucleosides and their use for the synthesis of oligonucleotides. These derivatives are in accordance with the formula: (I) in which B represents a radical derived from guanine, cytosine or adenine, whose exocylic NH group is protected by the group with R1 representing a hydrogen atom or a alkyl radical and R2 a hydrogen atom, and alkyl radical, an alkoxy radical and optionally substituted aryloxy radical, R3 represents a hydrogen atom, the dimethoxytrityl radical or the radical R4 represents a hydrogen atom, the radical of formula: or a radical suitable for the synthesis of polynucelotides and R5 represents a hydrogen atom or the protected or unprotected hydroxyl OH radical.

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.