CAS: 76101-30-9; 3-Dichlorophosphanyloxypropanenitrile

该化合物是一种高度活性有机磷化合物,主要用作磷酸盐和磷酸盐衍生物合成的关键中间体,其二氯化二甲二醇功能可产生高效磷酸反应,使其在寡甲二烯酸酯和核分子酸化学中具有价值,2-丙基乙酸组在合成期间具有更强的稳定性,同时在温和条件下很容易地重新移动.该试剂对于磷米地进行固相DNA和RNA合成尤其有用.其反应性和选择性使得它成为研究和工业应用中受控磷酸过程的首选,确保由此产生的产品的高产量和纯度.

结构式图片

合成工艺路线路线简述

  • 合成目标产物 2-Cyanoethyl Phosphorodichloridite 主要起始原料 3-(Trimethylsilyloxy)Propionitrile
  • (文献来源)合成步骤主要原料 3-(Trimethylsilyloxy)Propionitrile
📜3-羟基丙腈置于n,N-二异丙基乙胺,1-丁基-3-甲基咪唑二(三氟甲基磺酰)酰亚胺,三氯化磷体系中,化学反应 0.5H,反应生成 2-氰乙基二氯磷酸酯
参考文献:使用离子液体选择性合成氯代亚磷酰胺
标题:使用离子液体选择性合成氯代亚磷酰胺
摘要:一系列的氯代亚磷酰胺已经被制备出来. 离子液体 并与分子合成的材料进行比较 溶剂.通过使用离子液体作为反应介质,湿气敏感性和杂质问题困扰了现有的传统合成路线,现已得到缓解.不仅可以不使用库存化学品纯化,但是反应可以在室温和高浓度下进行.此外,减少了反应时间,并且可以在保持对产物选择性的严格控制的同时快速添加试剂.除了它们作为反应介质的作用之外,离子液体 还为这些对水分高度敏感的氯代亚磷酰胺提供了独特的存储介质.
DOI:10.1039/b905000K

海关参考信息

专利信息


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: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.

专利号:US-10730904-B2
优先权日:2012-11-14
标 题:Method for liquid-phase synthesis of nucleic acid
发明人:NONOGAWA MITSURU; NAGATA TOSHIAKI; SAITO HIDEKI; YASUMA TSUNEO
权利人:TAKEDA PHARMACEUTICALS CO
摘要:In this method, an oligonucleotide represented by formula (II) [wherein Y 1 , Q, Base, r and r′ are each as defined in claim 1 ] is prepared by using, as a synthesis unit, a novel nucleoside monomer compound represented by formula (I) [wherein X, R 1 , Y, Base, Z, Ar, R 2 , R 3 and n are each as defined in claim 1 ]. The novel nucleoside monomer compound is a nucleoside, the base moiety of which is substituted with an aromatic-hydrocarbon-ring-carbonyl or -thiocarbonyl group having at least one hydrophobic group. The method can dispense with column-chromatographic purification in every reaction, and enables base elongation not only in the 3′-direction but also in the 5′-direction, thus attaining efficient liquid-phase mass synthesis of an oligonucleotide.

专利号:US-6340749-B1
优先权日:1995-10-06
标题:Preparation of nucleoside phosphoramidites and oligonucleotide synthesis
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 neutral or weakly basic conditions, without an additional activation step. 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.

专利号:US-5859233-A
优先权日:1996-02-21
标 题 :Synthons for synthesis of oligonucleotide N3-P5 phosphoramidates
发明人:HIRSCHBEIN BERNARD L; FEARON KAREN L; GRYAZNOV SERGEI M; MCCURDY SARAH N; NELSON JEFFREY S; SCHULTZ RONALD G
权利人:LYNX THERAPEUTICS INC
摘要:The invention provides a method of synthesizing oligonucleotide N3'->P5' phosphoramidates using an amine-exchange reaction of phosphoramidites in which a -deprotected 3'-amino group of a solid phase supported oligonucleotide chain is exhanged for the amino portion of a 5'-phosphoramidite of an incoming monomer which has a protected 3'-amino group. The resulting internucleotide phosphoramidite linkage is then oxidized to form a stable protected phosphoramidate linkage. The method of the invention greatly improves product yields and reduces reagent usage over currently available methods for synthesizing the above class of compound.

专利号:WO-9742208-A1
优先权日:1996-05-03
标题 :In situ preparation of nucleoside phosphoramidites and their use in synthesis of oligonucleotides

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品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

参考标题:Total Synthesis Of The Congested, Bisphosphorylated Morganella Morganii Zwitterionic Trisaccharide Repeating Unit
作者:D. Jamin Keith,Steven D. Townsend |发布日期:2019.8.14
摘要:Zwitterionic Polysaccharides (Zps) Activate T-Cell-Dependent Immune Responses By Major Histocompatibility Complex Class Ii Presentation. Herein, We Report The First Synthesis Of A Morganella Morganii Zps Repeating Unit As An Enabling Tool In The Synthesis Of Novel Zps Materials. The Repeating Unit Incorporates A 1,2-Cis--Glycosidic Bond; The Problematic 1,2-Trans-Galactosidic Bond, Gal-β(1->3)-Galnac;

合成参考文献


摘要:Stankevič, M.; Pietrusiewicz, K. M., Science of Synthesis, (2009) 42, 310.
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