CAS: 89992-70-1; 3-((Chloro(Diisopropylamino)Phosphanyl)Oxy)Propanenitrile

该化合物是一种高活性磷胺试剂,通常用于寡甲二烯二酸合成,其主要优点包括:由于丙烯二烯乙基保护组可以最大限度地减少磷酸二硝基试管形成过程中的侧反应,因此加强了稳定性;二异丙基胺会进一步提高结合步骤的选择性和效率;该化合物在自动固态阶段DNA/RNA合成中特别有用,与非丙基类相比,具有高产量,对水解的敏感度降低;它与标准的脱色和氧化议定书相兼容性,因此它成为生产高纯度寡苯二烯二甲酸酯的可靠选择;该异丙基苯并附最低副产品;该异丙基苯通常在水性条件下处理,以保持其再活动.

结构式图片

相似化合物

102691-36-1 102690-88-0 86030-43-5

欧盟法规

ECHA物质C&L通报

上下游产品

2-cyanoethyl phosphorodichloridite N,N-diisopropyl-1,1,1-trimethylsilylamine diisopropylamine N,N-diisopropylphosphoramide dichloride Thiophosphoric acid O,O'-bis-(2-cyano-ethyl) ester O''-((3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl) ester

合成工艺路线路线简述

  • 1006061-57-9 = 89992-70-1
    反应条件:1.1 Catalysts: Tris(2-Carboxyethyl)Phosphine,Copper (Tris(Benzyltriazolylmethyl)Amine Complexes),Tris[(1-Benzyl-1H-1,2,3-Triazol-4-Yl)Methyl]Amine (Copper Complexes) Solvents: Dimethyl Sulfoxide,Tert-Butanol,Water; 12 H,Rt
    标题:7-Deazapurine And 8-Aza-7-Deazapurine Nucleoside And Oligonucleotide Pyrene "Click" Conjugates: Synthesis,Nucleobase Controlled Fluorescence Quenching,And Duplex Stability
    作者:Ingale,Sachin A.; Pujari,Suresh S.; Sirivolu,Venkata Ramana; Ding,Ping; Xiong,Hai; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2012 卷标:77(1) 页码:188-199]

    76101-30-9 = 89992-70-1
    反应条件:1.1 Solvents: Diethyl Ether
    标题:2-Cyanoethyl Diisopropylchlorophosphoramidite
    作者:Beaucage,Serge L.
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2002 卷标:1 页码:1-6]

    76101-30-9 = 89992-70-1
    反应条件:1.1 30 Min,Rt
    标题:Selective Diphosphorylation,Dithiodiphosphorylation,Triphosphorylation,And Trithiotriphosphorylation Of Unprotected Carbohydrates And Nucleosides
    作者:Ahmadibeni,Yousef; Parang,Keykavous
    参考文献:Organic Letters 日期:2005 卷标:7(25) 页码:5589-5592]

    109-78-4 = 89992-70-1
    反应条件:1.1 Solvents: Acetonitrile; Rt -> 0 °C1.2 Reagents: Phosphorus Trichloride; 2 H,0 °C; 0 °C -> Rt1.3 Solvents: Diethyl Ether; Rt1.4 12 H,Rt
    标题:Synthesis Of Cyclic Di-Nucleotidic Acids As Potential Inhibitors Targeting Diguanylate Cyclase
    作者:Ching,Shi Min; Tan,Wan Jun; Chua,Kim Lee; Lam,Yulin
    参考文献:Bioorganic & Medicinal Chemistry 日期:2010 卷标:18(18) 页码:6657-6665]

    76101-30-9 = 89992-70-1 [标题:Reaction Conditions
    标题:Synthesis Of Lipophilic Phosphate Triester Derivatives Of 5-Fluorouridine And Arabinocytidine As Anticancer Prodrugs
    作者:Le Bec,Christine; Huynh Dinh,Tam
    参考文献:Tetrahedron Letters 日期:1991 卷标:32(45) 页码:6553-6]

    109-78-4 = 89992-70-1
    反应条件:1.1 Reagents: Diisopropylethylamine,Phosphorus Trichloride Solvents: 1-Butyl-3-Methylimidazolium Bis(Trifluoromethylsulfonyl)Imide; 5 Min,Rt1.2 30 Min,Rt1.3 40 Min,Rt
    标题:Overcoming Hydrolytic Sensitivity And Low Solubility Of Phosphitylation Reagents By Combining Ionic Liquids With Mechanochemistry
    作者:Hardacre,Christopher; Huang,Haifeng; James,Stuart L.; Migaud,Marie E.; Norman,Sarah E.; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2011 卷标:47(20) 页码:5846-5848]

    = 89992-70-1
    反应条件:1.1 Reagents: 5′-O-[bis(4-Methoxyphenyl)Phenylmethyl]-2′-Deoxy-N-[6-[(9,10-Dihydro-9,10-Dioxo-...
    标题:α-β Chimeric Oligo-Dna Bearing Intercalator-Conjugated Nucleobase Inside The Linker Sequence Remarkably Improves Thermal Stability Of An Alternate-Stranded Triple Helix
    作者:Azam,A. T. M. Zafrul; Hasegawa,Minoru; Moriguchi,Tomohisa; Shinozuka,Kazuo
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2004 卷标:14(23) 页码:5747-5750
2-氰乙基二氯磷酸酯 反应生成 2-氰乙基n,N-二异丙基氯亚磷酰胺
参考文献:Gasparutto,D.;Molko,D.;Teoule,R.,Nucleosides And Nucleotides,9,(1990) N,C. 1087-1098
标题:Gasparutto,D.;Molko,D.;Teoule,R.,Nucleosides And Nucleotides,9,(1990) N,C. 1087-1098

海关参考信息

专利信息


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.

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-6531591-B1
优先权日:1999-07-07
标 题 :Synthesis of stable quinone and photoreactive ketone phosphoramidite reagents for solid phase synthesis of photoreactive-oligomer conjugates
发明人:FENSHOLDT JEF
权利人:EXIQON AS
摘要:Quinone phosphoramidite reagents as well as photoreactive ketone phosphoramidite reagents, such as anthraquinone phosphoramidite reagents and benzophenone phosphoramidite reagents were synthesized and used for the solid phase synthesis of photoreactive-oligonucleotide conjugates. These phosphoramidite reagents are stable, suitable for large-scale synthesis and designed for automated solid phase synthesis of oligomers terminating in a photoreactive moiety.

专利号:EP-1202998-B1
优先权日:1999-07-07
标 题 :Synthesis of stable quinone and photoreactive ketone phosphoramidite reagents for solid phase synthesis of photoreactive-oligomer conjugates
发明人:FENSHOLDT JEF
权利人:EXIQON AS
摘要:Quinone phosphoramidite reagents as well as photoreactive ketone phosphoramidite reagents, such as anthraquinone phosphoramidite reagents and benzophenone phosphoramidite reagents were synthesized and used for the solid phase synthesis of photoreactive-oligonucleotide conjugates. These phosphoramidite reagents are stable, suitable for large-scale synthesis and designed for automated solid phase synthesis of oligomers terminating in a photoreactive moiety.

专利号:US-12146136-B2
优先权日:2020-03-26
标题:Synthesis of modified oligonucleotides with increased stability
发明人:KHVOROVA ANASTASIA; ROUX LOÃ?C MAURICE RENÉ JEAN; YAMADA KEN
权利人:UNIV MASSACHUSETTS
摘要:This disclosure relates to the synthesis of novel modified oligonucleotides. The synthesis of novel phosphoramidites are also provided.

专利号:EP-0901500-B1
优先权日:1996-05-03
标题:In situ preparation of nucleoside phosphoramidites and their use in synthesis of oligonucleotides
发明人:ZHANG ZHAODA; TANG JIN-YAN
权利人:AVECIA BIOTECHNOLOGY INC
摘要:The invention provides novel bifunctional phosphitylating reagents and their application in in situ preparation of 5'-protected nucleoside phosphoramidites and synthesis of oligonucleotides. Bifunctional phosphitylating reagents according to the invention react quickly with nucleosides under weakly acidic conditions. In addition, the bifunctional phosphitylating reagents according to the invention generate chemoselectively the corresponding nucleoside phosphoramidites in situ, without need to purify the nucleoside phosphoramidites before using them in oligonucleotide synthesis. Finally, the bifunctional phosphitylating reagents according to the invention are relatively stable and easy to handle.
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主要参考文献

参考标题:Synthesis And Properties Of Aminoacylamido-Amp: Chemical Optimization For The Construction Of An N-Acyl Phosphoramidate Linkage
作者:Tomohisa Moriguchi,Terukazu Yanagi,Masao Kunimori,Takeshi Wada,Mitsuo Sekine |发布日期:2000.12.1
摘要:This Paper Describes The Design And Synthesis Of A New Type Of Aminoacyl-Adenylate Analogue (Aa-Ampn) Having An N-Acyl Phosphoramidate Linkage Where The Oxygen Atom Of The Mixed Anhydride Bond Of Aminoacyl-Adenylate (Aa-Amp) Is Replaced By An Amino Group. This New Type Of Aa-Amp Analogue Is Expected To Be Useful As Material For Studies On The Recognition Mechanism Of The Aminoacylation Of Trna And

合成参考文献


摘要:Stankevič, M.; Pietrusiewicz, K. M., Science of Synthesis, (2009) 42, 304.
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