CAS: 86061-01-0; Fmoc-Asp(Otbu)-Opfp

该化合物是一种化学化合物,通常用于peptide合成和有机化学,它是Apartic酸的衍生物,氨基酸受Fmoc(9-氟辛基碳基)组的保护,氨基酸为固态聚氨酯(OtBu)的稳定性和易于处理.OPfp注意到存在五氟苯(Pfp)酯,该酯经常作为分离组在组合反应中使用.该化合物的特点是它有能力促进形成peptide联结,同时为反应功能组提供保护,使其在固态聚氨基苯基合成中具有价值.该化合物在各种条件下的稳定性,加上对Fmoc和OtBu组的解保护,使得对peptid的受控和高效合成.此外,五溴二苯醚组的存在加强了氨基酸的再活性.

结构式图片

相似化合物

200335-75-7 86061-04-3 200616-21-3

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报

上下游产品

2,3,4,5,6-pentafluorophenol Fm°C-(tBu)Asp-OH pentafluorophenyl trifloroacetate (9-fluorenyl)methyl pentafluorophenyl carbonate2Fm°C-Asp(t-Bu)-Phe-NH2 cholecystokinin-4 α-Fm°C-L-Asn-OPfpNα-Fm°C-L-Asn-OPfp α-(Fluoren-9-ylmethoxycarbonyl)-L-aspartic 4-Acid Chloride 1-pentafluorophenyl EsterNα-(Fluoren-9-ylmethoxycarbonyl)-L-aspartic 4-Acid Chloride 1-pentafluorophenyl Ester

合成工艺路线路线简述

  • 71989-14-5 + 771-61-9 = 86061-01-0
    反应条件:1.1 Reagents: Diisopropylethylamine,Morpholinium,4-(4,6-Dimethoxy-1,3,5-Triazin-2-Yl)-4-Methyl-,4-Methylbenzenesul... Solvents: Dichloromethane; 40 Min,0 °C1.2 Reagents: Diisopropylethylamine; 2 H,0 °C; Overnight,Rt
    标题:4-(4,6-Dimethoxy-1,3,5-Triazin-2-Yl)-4-Methylmorpholinium Toluene-4-Sulfonate (Dmt/nmm/tso-) Universal Coupling Reagent For Synthesis In Solution
    作者:Fraczyk,Justyna; Kaminski,Zbigniew J.; Katarzynska,Joanna; Kolesinska,Beata
    参考文献:Helvetica Chimica Acta 日期:2018 卷标:101(1)]

    71989-14-5 + 771-61-9 = 86061-01-0
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Ethyl Acetate
    标题:9-Fluorenylmethyl Pentafluorophenyl Carbonate As A Useful Reagent For The Preparation Of N-[(9-Fluorenylmethoxy)Carbonyl] Amino Acids And Their Pentafluorophenyl Esters
    作者:Schon,Istvan; Kisfaludy,Lajos
    参考文献:Synthesis 日期:1986 卷标:(4) 页码:303-5]

    71989-14-5 + 14533-84-7 = 86061-01-0 [标题:Reaction Conditions
    标题:Preparation Of Pentafluorophenyl Esters Of Fmoc Protected Amino Acids With Pentafluorophenyl Trifluoroacetate
    作者:Green,Michael; Berman,Judd
    参考文献:Tetrahedron Letters 日期:1990 卷标:31(41) 页码:5851-2]

    71989-14-5 + 771-61-9 = 86061-01-0
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Ethyl Acetate
    标题:Preparation Of Glycosyl Amino Acids As Building Blocks For The Combinatorial Synthesis Of Neoglycoconjugates
    作者:Ziegler,Thomas; Roseling,Dirk; Subramanian,Lakshminarayanapuram R.
    参考文献:Tetrahedron: Asymmetry 日期:2002 卷标:13(9) 页码:911-914]

    71989-14-5 + 771-61-9 = 86061-01-0
    反应条件:1.1 Reagents: 4-Methylmorpholine,9-Fluorenylmethyl Chloroformate; 10 Min,-15 °C1.2 Solvents: Tetrahydrofuran; -15 °C -> Rt
    标题:9-Fluorenylmethyl Chloroformate (Fmoc-Cl) As A Useful Reagent For The Synthesis Of Pentafluorophenyl,2,4,5-Trichlorophenyl,Pentachlorophenyl,P-Nitrophenyl,O-Nitrophenyl And Succinimidyl Esters Of Nα-Urethane Protected Amino Acids
    作者:Tantry,Subramanyam J.; Babu,Vommina V. Suresh
    参考文献:Letters In Peptide Science 日期:2004 卷标:10(5-6) 页码:655-662]

    71989-14-5 + 771-61-9 = 86061-01-0
    反应条件:1.1 Reagents: 4-Methylmorpholine,4-(4,6-Dimethoxy-1,3,5-Triazin-2-Yl)-4-Methylmorpholinium Tetrafluoroborate Solvents: Acetonitrile; 2 H,0 °C1.2 Catalysts: 4-(Dimethylamino)Pyridine; 0.5 H,0 °C; 14 H,Rt
    标题:N-Triazinylammonium Tetrafluoroborates. A New Generation Of Efficient Coupling Reagents Useful For Peptide Synthesis
    作者:Kaminski,Zbigniew J.; Kolesinska,Beata; Kolesinska,Justyna; Sabatino,Giuseppina; Chelli,Mario; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2005 卷标:127(48) 页码:16912-16920
五氟苯酚置于n-甲基吗啉,4-(4,6-Dimethoxy-1,3,5-Triazin-2-yl)-4-Methylmorpholinium Toluene-4-Sulfonate体系中,用 乙腈 作为反应溶剂,化学反应 22.0H,以88%的收率获得产物fmoc-L-天冬氨酸-β-叔丁酯-Alpha-五氟苯酯
参考文献:P-Toluenosulfonate Salt Of N-Methyl-N-(3,5-Dimathoxy-2,4,6-Triazinyl-1-)-Morpholine And Related Compounds For Use As Condensing Reagent In Peptide Synthesis
标题:P-Toluenosulfonate Salt Of N-Methyl-N-(3,5-Dimathoxy-2,4,6-Triazinyl-1-)-Morpholine And Related Compounds For Use As Condensing Reagent In Peptide Synthesis

海关参考信息

专利信息


专利号:EP-1586566-B9
优先权日:2004-03-29
标 题:P-toluenosulfonate salt of N-Methyl-N-(3,5-dimathoxy-2,4,6-triazinyl-1-)-morpholine and related compounds for use as condensing reagent in peptide synthesis
发明人：KAMINSKI ZBIGNIEW; KOLESINSKA BEATA; KOLESINSKA JUSTYNA; JASTRZABEK KONRAD
权利人:POLITECHNIKA LODZKA; KAMINSKI ZBIGNIEW; KOLESINSKA BEATA
摘要:The invention refers to new quarternary N-(3,5-disubstituted-1,3,5-triazinyl-1)-ammonium salts of sulfonic acids, with formula 1, where R1 and R2 denote in total or independently a halogen atom, an alkyl group, a substituted alkyl group, an alkoxy group, a substituted alkoxy group, a cycloalcoxy group, a substituted cycloalkoxy group, an aryl group, a substituted aryl group, an aryloxy group, a substituted aryloxy group, a heterocyclic group or a substituted heterocyclic group, preferably the methoxy group, where R3, R4, R5 denote independently each other an alkyl group, a substituted alkyl group, a cycloalkyl group, a substituted cycloalkyl group, an aryl group, a substituted aryl group, a heterocyclic or a substituted heterocyclic group, or form a heterocyclic ring with nitrogen atom, whereas O-SO2R6 denotes a sulfate anion, hydrosulfonate anion, arylsulfonate anion, preferable benzenosulfonate anion, p-toluenosulfonate anion, p-bromobenzenosulfonate anion, p-chlorobenzenosulfonate anion, alkylosulfonate anion, preferable methanosulfonate and trifluoromethanesulfonate anions or amidosulfonate anion. The new compounds are designed for application as condensing reagents in syntheses of amides, esters, carboxylic acid hydroxides, and particularly in synthesis of peptides and their esters.

专利号:US-2011046349-A1
优先权日:2009-07-15
标题:Process for the production of exenatide and of an exenatide analogue
发明人：GIRAUD MATTHIEU; DROZ ANNE-SOPHIE; VARRAY STEPHANE; REKAI EL DJOUHAR; BRICHARD MARIE-HELENE; LATASSA DANIEL; DEVIJVER CHRISTINE; GILLES PASCAL; CAUVIN JEANNE-MARIE; ALBERICIO FERNANDO; BAS MARTA PARADIS
权利人:GIRAUD MATTHIEU; DROZ ANNE-SOPHIE; VARRAY STEPHANE; REKAI EL DJOUHAR; BRICHARD MARIE-HELENE; LATASSA DANIEL; DEVIJVER CHRISTINE; GILLES PASCAL; CAUVIN JEANNE-MARIE; ALBERICIO FERNANDO; BAS MARTA PARADIS
摘要:Exenatide, a polypeptide having the 39 amino acid sequence H-1His-Gly-Glu-Gly-5Thr-Phe-Thr-Ser-Asp-10Leu-Ser- Lys-Gln-Met-15Glu-Glu-Glu--Ala-Val-20Arg-Leu-Phe- Ile-Glu-25Trp-Leu-Lys-Asn-Gly-30Gly-Pro-Ser-Ser- Gly-35Ala--Pro-Pro-Pro-Ser-NH2, respectively its 44-mer analogue H-1His-Gly-Glu-Gly-5Thr-Phe-Thr-Ser-Asp-10Leu-Ser- Lys-Gln-Met-15Glu-Glu-Glu--Ala-Val-20Arg-Leu-Phe- Ile-Glu-25Trp-Leu-Lys-Asn-Gly-30Gly-Pro-Ser-Ser- Gly-35Ala--Pro-Pro-Ser-Lys-40Lys-Lys-Lys-Lys-Lys- NH2 is prepared via a convergent four-fragment synthesis strategy from the fragments comprising the amino acid positions 1-10, 11-21, 22-29 and 30-39, respectively 30-44.

专利号:EP-1586566-B1
优先权日:2004-03-29
标 题 :P-toluenosulfonate salt of N-Methyl-N-(3,5-dimathoxy-2,4,6-triazinyl-1-)-morpholine and related compounds for use as condensing reagent in peptide synthesis

专利号:EP-1586566-A1
优先权日:2004-03-29
标题:P-toluenosulfonate salt of N-Methyl-N-(3,5-dimathoxy-2,4,6-triazinyl-1-)-morpholine and related compounds for use as condensing reagent in peptide synthesis

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主要参考文献

参考标题:4-(4,6-Dimethoxy-1,3,5-Triazin-2-Yl)-4-Methylmorpholinium Toluene-4-Sulfonate (Dmt/nmm/tso− ) Universal Coupling Reagent For Synthesis In Solution
作者:Justyna Fraczyk,Zbigniew J. Kaminski,Joanna Katarzynska,Beata Kolesinska |发布日期:2018.1
摘要:Environmentally‐friendly N‐triazinylammonium Family Of Sulfonates, Has Been Found To Be A Very Effective Coupling Reagent For The Synthesis Of Amides, Esters And Peptides In Solution. This Study Confirms The Usefulness Of Dmt/nmm/tso− For Peptide Synthesis In Solution, Starting From Z‐, Fmoc‐, And Boc‐protected Substrates As Well As Unnatural Building Blocks. Peptide Synthesis With Dmt/nmm/tso− Produced

合成参考文献


摘要:Lubell, W. D.; Blankenship, J. W.; Fridkin, G.; Kaul, R., Science of Synthesis, (2005) 21, 750.
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