CAS: 2096-10-8; (2R,3R,4S,5R)-2-(2,6-Diamino-9H-Purin-9-yl)-5-(Hydroxymethyl)Tetrahydrofuran-3,4-Diol

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相似化合物

58-61-7 5536-17-4 3080-29-3

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上下游产品

1-phenylcyanamide 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile methanol 2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine 2-fluoroadenosine isoguanosine 2,6-diamino-9-(3-O-methyl-β-D-ribofuranosyl)purine 2-amino-2'-O-methyladenosine

合成工艺路线路线简述

  • 合成目标产物 2-Aminoadenosine 主要起始原料 Uridine And 2,6-Diaminopurine
  • (文献来源)合成步骤主要原料 Uridine 和 2,6-Diaminopurine
鸟苷置于palladium On Activated Charcoal 吡啶,Sodium Azide,四乙基氯化铵,氨,氢气,N,N-二甲基苯胺,三氯氧磷体系中,用 甲醇,N,N-二甲基甲酰胺,乙腈 用作溶剂,化学反应生成2-氨基腺嘌呤核苷
参考文献:氧化铜存在下钯催化偶合合成8-杂芳基取代的9-(β-D-呋喃核糖基)-2,6-二氨基嘌呤
标题:氧化铜存在下钯催化偶合合成8-杂芳基取代的9-(β-D-呋喃核糖基)-2,6-二氨基嘌呤
摘要:制备8-(2-和3-噻吩基)-2,6-二氨基嘌呤和8-(2-和3-呋喃基)-2,6-的9-(β-D-呋喃呋喃糖基)衍生物的简便方法已经研究出潜在的抗病毒药物二氨基嘌呤.关键步骤是在2-和3-三丁基锡烷基噻吩与2-和3-三丁基锡烷基呋喃和三甲基甲硅烷基保护的9-(β-D-呋喃呋喃糖基)-2,6-二氨基-8-溴-之间进行pd(0)催化的stille偶联.嘌呤.为了获得快速反应和高收率,必须使用n,N-二甲基甲酰胺在110°下作用作溶剂,并使用二氧化(二苯基膦-丙烷)钯(II)[pdcl 2(dppp)]与氧化铜作为共试剂. .
Doi:10.1002/jhet.5570320331

海关参考信息

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-6048975-A
优先权日:1991-09-12
标 题:Process for the chemical synthesis of oligonucleotides
发明人:PFLEIDERER WOLFGANG; BERGMANN FRANK
权利人:HOECHST AG
摘要:A process for the chemical synthesis of oligonucleotides n Use of a dansylethoxycarbonyl group as base-labile 5'-hydroxyl protective group in the chemical synthesis of DNA and RNA and suitable synthetic processes. n The ease of detection of the dansyl protective group and the ease of elimination from the sugar residue of the nucleotide without side reactions make oligonucleotide synthesis possible with high yields in very small quantities.

专利号:US-10167308-B2
优先权日:2013-09-14
标题:Highly efficient synthesis of long RNA using reverse direction approach
发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:CHEMGENES CORP
摘要:The present invention relates to novel process of reverse 5′→3′ directed synthesis of RNA oligomers in the range of about 100-mer to about 200-mer has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.

专利号:US-5945524-A
优先权日:1990-09-14
标 题 :Process for the chemical synthesis of oligonucleotides
发明人:PFLEIDERER WOLFGANG; BERGMANN FRANK
权利人:HOECHST AG
摘要:Use of a dansylethoxycarbonyl group as base-labile 5'-hydroxyl protective group in the chemical synthesis of DNA and RNA and suitable synthetic processes. n The ease of detection of the dansyl protective group and the ease of elimination from the sugar residue of the nucleotide without side reactions make oligonucleotide synthesis possible with high yields in very small quantities.

专利号:US-2020239921-A1
优先权日:2016-02-03
标 题 :Chemoenzymatic synthesis of s-nucleosyl amino acids (sna), analogs of s-adenosyl-l-methionine and s-adenosyl-l- homocysteine and uses thereof
发明人:BURGOS EMMANUEL SEBASTIEN; SHECHTER DAVID
权利人:ALBERT EINSTEIN COLLEGE MEDICINE
摘要:Disclosed are methods for chemoenzymatic synthesis of S-Nucleosyl Amino acid probes (SNA), analogs of S-adeno-syl-L-methionine and S-adenosyl-L-homo-cysteine, analogs synthesized by the methods, and uses thereof.
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主要参考文献


1: Grzeskowiak K, Webb TR, Orgel LE. Template-directed synthesis with 2-aminoadenosine. J Mol Evol. 1984;21(1):81-3. doi: 10.1007/BF02100631. 25(3):307-14. doi: 10.1080/15257770500544529. 79(10):4423-37. doi: 10.1021/jo500392j. Epub 2014 Apr 18. 5(18):3034-45. doi: 10.1039/b708736e. Epub 2007 Aug 14. 71(1):81-90. doi: 10.1021/jo0516640. 19(12):3193-8. doi: 10.1093/nar/19.12.3193.
7: Kaloudis P, D'Angelantonio M, Guerra M, Gimisis T, Mulazzani QG, Chatgilialoglu C. One-electron reduction of 8-bromo-2-aminoadenosine in the aqueous phase: radiation chemical and DFT studies of the mechanism. J Phys Chem B. 2008 Apr 24;112(16):5209-17. doi: 10.1021/jp800480f. Epub 2008 Mar 29. 154(2):259-65. doi: 10.1111/j.1432-1033.1986.tb09391.x. 34(4):1340-4. doi: 10.1021/jm00108a015.

合成参考文献


参考文献:10.1021/jm200650j
摘要:Murakami E, Bao H, Mosley RT, Du J, Sofia MJ, Furman PA. Adenosine Deaminase-like Protein 1 (ADAL1): Characterization and Substrate Specificity in the Hydrolysis of N6- or O6-Substituted Purine or 2-Aminopurine Nucleoside Monophosphates. J. Med. Chem. 2011 Jul 22;54(16):5902–14. doi: 10.1021/jm200650j.
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