CAS: 3083-77-0; 1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)Pyrimidine-2,4(1H,3H)-Dione

该化合物是一个核分子模拟物,与生化和制药研究密切相关.其结构以与极地有关的阿拉伯铀酸糖协会为特征,使其成为改良核酸和抗病毒化合物合成中的宝贵中间体.该化合物特别有助于研究酶-基相互作用,特别是与核分子磷素和运动酶的相互作用,因为它的立体特征.其稳定性和明确界定的化学特性有利于精确的实验应用,包括机械学研究和药物开发.研究者认为,核分子新陈代谢和设计针对病毒或细胞核酸途径的潜在治疗剂的作用是1-beta-D-Arabinouranosuranicil.

结构式图片

相似化合物

3258-07-9 2140-76-3 4105-38-8

欧盟法规

ECHA物质C&L通报REACH预注册

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CAS号3736-77-4 2,2'-脱水尿苷 | CAS号58-96-8 尿苷 | CAS号87186-13-8 2,2'-Anhydrouri... | CAS号506-68-3 溴化氰 | CAS号847650-91-3 1-((2R,4S,5R)-3... | CAS号10212-25-6 盐酸环胞苷 | CAS号14057-18-2 2,4(1H,3H)-Pyri... | CAS号1024-99-3 5-碘尿苷 | CAS号28309-53-7 2α-(Acetoxymeth... | CAS号66-22-8 尿嘧啶 | CAS号34079-68-0 2-氨基阿糖腺苷 | CAS号30100-83-5 2,4(1H,3H)-Pyri... | CAS号25130-27-2 2(1H)-Pyrimidin... | CAS号605-23-2 阿糖胸苷 | CAS号5536-17-4 阿糖腺苷 | CAS号146-78-1 2-氟腺苷 | CAS号32976-84-4 2-amino-9-[3,4-... | CAS号3052-06-0 2,4(1H,3H)-Pyri... | CAS号34793-14-1 [3,4-diacetylox...

合成工艺路线路线简述

  • 合成目标产物 1-Beta-D-Arabinofuranosyluracil 主要起始原料 Cytarabine
  • (文献来源)合成步骤主要原料 Cytarabine
尿嘧啶核苷置于碳酸二苯酯,碳酸氢钠,三乙胺体系中,用 六甲基磷酰三胺,水 用作溶剂,化学反应 5.33H,反应生成阿糖尿苷
参考文献:4-(1,2,4-三唑-1-基)-和4-(3-硝基-1,2,4-三唑-1-基)-1-(β-D-2,3,5-三-O-乙酰基阿拉伯呋喃糖基)嘧啶-2(1 H)-Ones.1-(β-D-阿拉伯呋喃糖基)胞嘧啶(ara-C)衍生物的合成中的重要中间体
标题:4-(1,2,4-三唑-1-基)-和4-(3-硝基-1,2,4-三唑-1-基)-1-(β-D-2,3,5-三-O-乙酰基阿拉伯呋喃糖基)嘧啶-2(1 H)-Ones.1-(β-D-阿拉伯呋喃糖基)胞嘧啶(ara-C)衍生物的合成中的重要中间体
摘要:用三(1 H-1,2,4-三唑-1-基)膦氧化物处理尿苷制得的乙酰化衍生物(3B),其总收率为86%,得到高产率的化合物(6A),和用3-硝基-1,2,4-三唑和二苯基氯代磷酸酯以高收率得到化合物(6B).当在室温下使前一种产物(6A)与氨,甲胺,二甲胺和吗啉反应,并且必要时将产物进一步脱乙酰基时,Ara-C(1; R 1 = R 2 = H)及其对应的4-ñ-烷基衍生物(1; R 1 = H,R 2 = Me)时,(1; R 1 = R 2 = Me)和[1; R 1,R 2 =-(ch2) 2 O(ch 2) 2-]的收率很高.当化合物(6A)或(6B)与苯胺在吡啶溶液中加热,然后产物脱乙酰化时,以高收率获得4-N-苯基-芳族-C(1; R 1= H,R 2= Ph).将硝基化合物(6B)转化为ara-C衍生物(1; R 1 = H,R 2 = Ch 2 Co 2 Me)
Doi:10.1039/p19820001171

海关参考信息

专利信息


专利号:US-9920084-B2
优先权日:2011-08-23
标题 :Ionic tags for synthesis of oligoribonucleotides
发明人:DAMHA MASAD J; HASSLER MATTHEW; CHAN TAK-HANG; NANDYALA MALLIKARJUNA REDDY; DONGA ROBERT ALEXANDER
权利人:DAMHA MASAD J; HASSLER MATTHEW; CHAN TAK HANG; NANDYALA MALLIKARJUNA REDDY; DONGA ROBERT ALEXANDER; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIV; HONG KONG POLYTECHNIC UNIV
摘要:The invention relates to the chemical synthesis of oligonucleotides, e.g., oligoribonucleotides. In another aspect, the invention relates to compounds of formula (II) processes for making these compounds, and the use thereof in the chemical synthesis of oligonucleotides, e.g., oligoribonucleotides. The invention also relates to methods of synthesis of oligomers, including but not limited to oligopeptides, oligosaccharides and oligonucleotides, particularly oligoribonucleotides and also oligodeoxyribonucleotides, in solution systems, and ionic tag linkers for use in methods provided herein.

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-5824472-A
优先权日:1986-03-24
标 题 :Process for the synthesis of sugar nucleotides using recombinant-DNA methods
发明人:BETLACH MICHAEL R; DOHERTY DANIEL H; VANDERSLICE REBECCA W
权利人:MONSANTO CO
摘要:A recombinant-DNA mediated method for the synthesis of sugar nucleotides is disclosed. This method utilizes portable DNA sequences capable of directing the microbial synthesis of various enzymes that catalyze the synthesis of sugar nucleotides, including UDP-glucose, UDP-glucuronic acid and GDP-mannose. The sugar moieties of these sugar nucleotides may subsequently be incorporated into industrially-useful polysaccharides such as xanthan gum. It has been found that vectors containing the portable DNA sequences described herein are capable both of causing sugar nucleotide production in microorganisms previously incapable of such synthesis and of causing increased sugar nucleotide production in organisms capable of synthesizing small quantities of these compounds. In particular, plasmids pAS7, pAS9 and pTS13 are disclosed. These plasmids are capable of directing sugar nucleotide synthesis in various hosts, including Xanthomonas sp. such as X. campestris and other organisms such as E. coli and various Pseudomonas sp.

专利号:US-2023235372-A1
优先权日:2020-06-12
标题:Ab-initio, template-independent synthesis of nucleic acids using thermostable enzymes
发明人:RANDRIANJATOVO-GBALOU IRINA; SAID AHMED; RAHIER RENAUD
权利人:SYNHELIX
摘要:The invention relates to the field of nucleic acid synthesis or sequencing, more specifically to methods for ab-initio synthesis of nucleic acids, comprising contacting a nucleotide with a free 3′-hydroxyl group, with at least one nucleoside triphosphate, or a combination of nucleoside triphosphates, in the presence of an archaeal DNA primase or a functionally active fragment and/or variant thereof, thereby covalently binding said nucleoside triphosphate to the free 3′-hydroxyl group of the nucleotide. It also relates to isolated functionally active fragments of archaeal DNA primases which are capable of both ab-initio single-stranded nucleic acid synthesis activity and template-independent terminal nucleotidyl transferase activity.

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-8138330-B2
优先权日:2006-09-11
标 题 :Process for the synthesis of oligonucleotides
发明人:LEUCK MICHAEL; WOLTER ANDREAS; STUMPE ALFRED
权利人:LEUCK MICHAEL; WOLTER ANDREAS; STUMPE ALFRED; SIGMA ALDRICH CO LLC
摘要:The present invention discloses novel methods for the synthesis of oligonucleotides with nucleoside phosphoramidites on solid supports. The methods comprise the stepwise chain assembly of oligonucleotides on supports with 5′-acyl phosphoramidites. The synthesis cycles consist of a front end deprotection step which is conducted with a solution of a primary amine or a phenolate, a phosphoramidite coupling step with a 5′-acyl nucleoside phosphoramidite in the presence of an activator, a phosphite oxidation step and an optional capping step. The novel methods improve the quality of synthetic oligonucleotides due to the irreversibility of the front end deprotection step, which prevents the formation of deletion sequences, and due to the avoidance of acidic reagents in the synthesis cycles, which prevent the formation of depurination side products. The invention further discloses novel nucleoside phosphoramidite compositions wherein the phosphoramidites carry acyl front end protective groups which are cleavable with primary amines or phenolates. The invention is applicable to the synthesis of oligodeoxyribonucleotides, oligoribonucleotides and oligonucleotides with modifications in their sugar or phosphate groups.
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1: Bertin MJ, Schwartz SL, Lee J, Korobeynikov A, Dorrestein PC, Gerwick L, Gerwick WH. Spongosine production by a Vibrio harveyi strain associated with the sponge Tectitethya crypta. J Nat Prod. 2015 Mar 27;78(3):493-9. doi: 10.1021/np5009762. Epub 2015 Feb 10.
2: Yoshikawa T, Kimura S, Hatano T, Okamoto K, Hayatsu H, Arimoto-Kobayashi S. Pseudouridine, an antimutagenic substance in beer towards N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). Food Chem Toxicol. 2002 Aug;40(8):1165-70.

合成参考文献


摘要:von Angerer, S., Science of Synthesis Knowledge Updates, (2011) 1, 103.
摘要:Kashemirov, B. A.; Błażewska, K.; Justyna, K.; Lyu, J.; McKenna, C. E., Science of Synthesis Knowledge Updates, (2021) 1, 424.
摘要:Kashemirov, B. A.; Błażewska, K.; Justyna, K.; Lyu, J.; McKenna, C. E., Science of Synthesis Knowledge Updates, (2021) 1, 334.
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