CAS: 102690-88-0; Bis(2-Cyanoethyl) Diisopropylphosphoramidite

该化合物是主要用于有机合成领域的化学化合物,特别是用于合成寡核素核素的合成,其特征是磷米基结构,其中包括将磷原子粘结在两个异丙基组和两个丙基基组,该化合物一般没有色素,可粉黄液体,以其反应性闻名,特别是有核素存在,使其成为磷酰胺化学中有价值的试剂,其功能使得核素有效结合,便利在核酸合成中形成磷化物联结,该复合物对湿度敏感,应在水分条件下处理,以防止水解.此外,必须指出,在处理该物质时,应采取适当的安全措施,因为如果吸入或浸入,可能会对健康造成危害.总体而言,BIS(2CYANOETYYL)-N,N-DIISOPROPYL PHOPRAMIDISTITE是分子生物学和遗传工程应用中的关键再试剂.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

N,N-diisopropylphosphoramide dichloride 3-Hydroxypropionitrile N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphineBis(2-cyanoethyl) 1-(4-methoxyphenyl)-2-oxo-2-phenylethyl phosphate Phosphoric acid bis-(2-cyano-ethyl) ester phenyl-(2-phenyl-[1,3]dioxolan-2-yl)-methyl ester Phosphorous acid bis-(2-cyano-ethyl) ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester Phosphorous acid bis-(2-cyano-ethyl) ester (1R,2S,3S,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester

合成工艺路线路线简述

  • 合成目标产物 Bis(2-Cyanoethyl)-N,N-Diisopropyl Phosphoramidite 主要起始原料 Diisopropylphosphoramidous Dichloride And 3-Hydroxypropionitrile
  • (文献来源)合成步骤主要原料 Diisopropylphosphoramidous Dichloride 和 3-Hydroxypropionitrile
二异丙胺置于n,N-二异丙基乙胺,三氯化磷体系中,用 乙醚,二氯甲烷 用作溶剂,化学反应生成双(2-氰乙基)-N,N-二异丙基亚磷酰胺
参考文献:Design And Synthesis Of Biotinylated Inositol 1,3,4,5-Tetrakisphosphate Targeting Grp1 Pleckstrin Homology Domain
标题:Design And Synthesis Of Biotinylated Inositol 1,3,4,5-Tetrakisphosphate Targeting Grp1 Pleckstrin Homology Domain
摘要:A Bifunctional Molecule Containing Biotin And D-Myo-Inositol 1,3,4,5-Tetrakisphosphate Was Synthesized. This Molecule Was Designed On The Basis Of X-Ray Structure Of The Complex Of D-Myo-Inositol 1,3,4,5-Tetrakisphosphates,Ins(1,3,4,5)P-4,And Grp1 Ph (General Receptor Of Phosphoinositides Pleckstrin Homology) Domain For The Application To The Widely Employed Biotin-Avidin Techniques. The Building Block Of Inositol Moiety Was Synthesized Starting With Myo-Inositol And Assembled With The Biotin-Linker Moiety Through A Phosphate Linkage. The Equilibrium Dissociation Constant K-D Of Biotinylated Ins(1,3,4,5)P-4 Binding Of Original Grp1 Ph Domain Was 0.14 Mu M In Pull-Down Analysis,Which Was Comparable To That Of Unmodified Ins(1,3,4,5)P-4. Furthermore,Biotinylated Ins(1,3,4,5)P-4 Had An Ability To Distinguish Grp1 Ph Domain From Plc Delta(1) Ph Domain. Thus,Biotinylated Ins(1,3,4,5)P-4 Retained The Binding Affinity And Selectivity Of Original Grp1 Ph Domain,And Realized The Intracellular Ins(1,3,4,5)P-4 Despite A Tethering At The 1-Phosphate Group Of Inositol. (C) 2011 Elsevier Ltd. All Rights Reserved.
Doi:10.1016/j.Bmc.2011.09.035

专利信息


专利号:US-11938187-B2
优先权日:2021-06-10
标题:Methods and compositions for synthesis of two-photon cleavable phosphoramidite molecules for oligonucleotide conjugation
发明人:LO PEGGY PIK KWAN; LIU LING SUM; TAM DICK YAN
权利人:UNIV CITY HONG KONG
摘要:The syntheses of two phosphoramidite building blocks based on BNSF and BNSMB structures are disclosed. Furthermore, some common molecular intermediates have been designed and linked to the central biphenyl core of the two molecules, resulting in a versatile and cost-effective design. These compounds can be effectively introduced to DNA oligonucleotides via the well-established standard cyanoethylphosphoramidite chemistry on the nucleic acid synthesizer. Fragmentation of these BNSF- and BNSMB-functionalized DNA strands is achieved by both one-photon and two-photon photolysis of photoliable bonds of [2-(2-nitrophenyl)propoxy]carbonyl groups on BNSF and BNSMB molecules respectively, resulting in two short pieces of single-stranded DNAs. The versatile design and facile synthesis of these two-photon photocleavage phosphoramidite molecules are beneficial to synthetic chemists and photochemists for the development of new caged compounds which enables to introduce into oligonucleotides as light-triggered carriers via solid-phase synthesis for a wide range of applications in materials science, polymer, chemistry, biology and DNA nanoecthnology.

专利号:US-2024092821-A1
优先权日:2020-03-31
标题:Synthesis of oligonucleotides and related compounds
发明人:ZHONG MINGHONG; JIN YI; GALA DINESH; PRHAVC MARIJA
权利人:JANSSEN BIOPHARMA INC
摘要:Methods of synthesizing oligonucleotides via new intermediates on a cleavable support having an azidomethyl moiety are disclosed. The method comprises multiple reaction cycles, each of which comprises sequential coupling a nucleoside or oligonucleotide subunit on a cleavable support having an azidomethyl moiety and a nucleoside phosphoramidite or an oligonucleotide phosphoramidite, capping, oxidation/thiolation and deblocking; followed by orthogonal cleavage of the azidomethyl support while keeping all other protecting groups intact. The method can be used in combination with a support moiety for either solid phase or liquid phase oligo synthesis. The soluble support facilitates homogeneous reactions and efficient separations by simple precipitation. The methods also provide novel intermediates useful in the synthesis of oligonucleotide conjugates.

专利号:US-7705136-B2
优先权日:2005-02-25
标 题 :Synthesis of 3′-, or 5′-, or internal methacrylamido-modified oligonucleotides
发明人:GOLOVA JULIA B; CHERNOV BORIS K
权利人:UCHICAGO ARGONNE LLC
摘要:New modifiers were synthesized for incorporation of a methacrylic function in 3′-, 5′- and internal positions of oligonucleotides during solid phase synthesis. A modifier was used for synthesis of 5′-methacrylated oligonucleotides for preparation of microarrays by a co-polymerization method.

专利号:US-6646118-B2
优先权日:1996-08-30
标 题 :Solid phase synthesis
发明人:KWIATKOWSKI MAREK; NILSSON MATS; LANDEGREN ULF
权利人:QUIATECH AB
摘要:The present invention relates to a support system for solid phase synthesis of oligomers, such as oligonucleotides, wherein the starting compound is bound to the support via a disiloxyl linkage. Furthermore, the invention relates to a method for synthesis of oligonucleotides on a solid support. The support system comprises a stable disiloxyl linkage providing high nucleoside loadings to the support and the method allows convenient non-laborious oligomer synthesis.

专利号:WO-2025037891-A1
优先权日:2023-08-14
标题:Oligonucleotide for 5'-capped rna synthesis
发明人:KIM KYUNGJIN; KIM UK-IL; KIM DAYOUNG; CHOI KANG HYUN; KIM JI SU
权利人:ST PHARM CO LTD
摘要:The present invention relates to a novel oligonucleotide primer used for the synthesis of 5'-capped RNA. The novel oligonucleotide primer for RNA capping, represented by chemical formula 1 in the present invention, can be usefully utilized in the fields of nucleic acid therapeutic agents or vaccines.

专利号:US-2023220381-A1
优先权日:2020-06-30
标 题 :Dna-encoded functionalized aptamers
发明人:SLEIMAN HANADI; LACROIX DE VIMEUR DE ROCHAME DONATIEN PHILIPPE MARIE; MCKEAGUE MAUREEN; HIRKA SERHII; SALIBA DANIEL; ANDERSON SHAUN IAN
权利人:THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING / MCGILL UNIV
摘要:It is provided the synthesis of an aptamer-like encoded oligomer (ALEnOmer), method of producing same and method of preparing a library of ALEnOmes. More particularly, the method of preparing ALEnOmer comprises coupling at least one phosphoramidite monomer with an orthogonal protecting group, and the ALEnOmer produces comprises a DNA coding strand covalently attached to an oligomer through a branching unit, wherein the oligomer has a degree of polymerization at least 5 and is an aptamer.
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合成参考文献


摘要:Kashemirov, B. A.; Błażewska, K.; Justyna, K.; Lyu, J.; McKenna, C. E., Science of Synthesis Knowledge Updates, (2021) 1, 336.
摘要:Kashemirov, B. A.; Błażewska, K.; Justyna, K.; Lyu, J.; McKenna, C. E., Science of Synthesis Knowledge Updates, (2021) 1, 420.
参考文献:10.1007/bf00731442
摘要:Martin TJ, Dufner G, Kratzer B, Schmidt RR. Ceramide-1-phosphate sugars: new types of glycophospholipids. Glycoconj J. 1996 Aug;13(4):547–53. doi: 10.1007/bf00731442.
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