CAS: 95687-41-5; Benzyl (2S,4R)-4-Hydroxy-2-(Hydroxymethyl)Pyrrolidine-1-Carboxylate

该化合物其结构特征为该化合物其结构特征为氨基酸,其特征为碳苯基(Cbz)保护组,该组增强了其稳定性和溶性,使其在各种合成应用中有所助益." Trans"配置表明,氢氧基组相对于干柱的具体空间安排,该组在生化环境中可影响其再活动与互动.Cbz-Trans-4-Hydroxy-L-polinol,由于其参与各种组合反应的能力,常常被用作有机化学中的一环形构件.其氢结合潜力由氢组成,影响其溶解性和不同溶剂的再活性.

结构式图片

物理性质

MSDS等安全信息

上下游产品

CAS号13504-85-3 CBZ-L-羟脯氨酸 | CAS号64187-48-0 N-CBZ-羟脯氨酸甲酯 | CAS号209269-34-1 N-CBZ-L-hydroxy... | CAS号51-35-4 L-羟脯氨酸 | CAS号501-53-1 氯甲酸苄酯

合成工艺路线路线简述

  • 合成目标产物 Z-Trans-4-Hydroxy-L-Prolinol 主要起始原料 Z-Hyp-Ome
  • 64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Tetrahydrofuran,Water; 2 H,17 °C; 1 H,17 °C; 2 H,17 °C; 5 H,17 °C; 12 H,23 °C; 23 °C -> 5 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H
    标题:Practical Gram-Scale Synthesis Of Iboxamycin,A Potent Antibiotic Candidate
    作者:Mason,Jeremy D.; Terwilliger,Daniel W.; Pote,Aditya R.; Myers,Andrew G.
    参考文献:Journal Of The American Chemical Society 日期:2021 卷标:143(29) 页码:11019-11025]

    13504-85-3 = 95687-41-5
    反应条件:1.1 Reagents: (Dimethyl Sulfide)Trihydroboron Solvents: Tetrahydrofuran; 0 °C; < 10 °C; 19 H,40 °C
    标题:An Immucillin-Based Transition-State-Analogous Inhibitor Of Trna-Guanine Transglycosylase (Tgt)
    作者:Hohn,Christoph; Haertsch,Adrian; Ehrmann,Frederik Rainer; Pfaffeneder,Toni; Trapp,Nils; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(20) 页码:6750-6754]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Ethanol,Tetrahydrofuran; 1.5 H1.2 Solvents: Ethanol; Overnight,Rt1.3 Reagents: Ammonium Chloride Solvents: Water; Ph 7
    标题:Backbone Extended Pyrrolidine Pna (Beppna): A Chiral Pna For Selective Rna Recognition
    作者:Govindaraju,T.; Kumar,Vaijayanti A.
    参考文献:Tetrahedron 日期:2006 卷标:62(10) 页码:2321-2330]

    16217-15-5 = 95687-41-5 + 64187-48-0 + 57653-35-7
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Tetrahydrofuran,Water
    标题:Carboxy Mediated Stereoselective Reduction Of Ketones With Sodium Triacetoxyborohydride: Synthesis Of Novel 3,4-Fused Tetrahydropyran And Tetrahydrofuran Prolines
    作者:Liu,Yi-Tsung; Wong,Jesse K.; Tao,Meng; Osterman,Rebecca; Sannigrahi,Mousumi; Et Al
    参考文献:Tetrahedron Letters 日期:2004 卷标:45(32) 页码:6097-6100]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Borohydride Solvents: Tetrahydrofuran
    标题:Effect Of C2-Exo Unsaturation On The Cytotoxicity And Dna-Binding Reactivity Of Pyrrolo[2,1-C][1,4]Benzodiazepines
    作者:Gregson,Stephen J.; Howard,Philip W.; Corcoran,Kathryn E.; Barcella,Simona; Yasin,Maqsood M.; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2000 卷标:10(16) 页码:1845-1847]

    = 95687-41-5 [标题:Reaction Conditions
    标题:Acridine- And Cholesterol-Derivatized Solid Supports For Improved Synthesis Of 3'-Modified Oligonucleotides
    作者:Reed,Michael W.; Adams,A. David; Nelson,Jeffrey S.; Meyer,Rich B. Jr.
    参考文献:Bioconjugate Chemistry 日期:1991 卷标:2(4) 页码:217-25]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Tetrahydrofuran,Water; 0 °C; 1 H,17 °C; 5 H,17 °C
    标题:Design,Synthesis,And Bioevaluation Of A Novel Hybrid Molecular Pyrrolobenzodiazepine-Anthracenecarboxyimide As A Payload For Antibody-Drug Conjugate
    作者:Lai,Weirong; Zhao,Shengyan; Lai,Qinhuai; Zhou,Wei; Wu,Mengdan; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2022 卷标:65(17) 页码:11679-11702]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Tetrahydrofuran,Water; 17 °C; 5 H,17 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; < 15 °C1.3 Reagents: Sodium Bicarbonate Solvents: Water; Ph 7 - 8
    标题:Scale-Up Synthesis Of Tesirine
    作者:Tiberghien,Arnaud C.; Von Bulow,Christina; Barry,Conor; Ge,Huajun; Noti,Christian; Et Al
    参考文献:Organic Process Research & Development 日期:2018 卷标:22(9) 页码:1241-1256]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Borohydride Solvents: Tetrahydrofuran; 0 °C; Overnight,Rt1.2 Reagents: Water; 2 H,0 °C
    标题:New Optically Active 4-Alkoxyprolinol Ethers Derived From Trans-4-Hydroxy-L-Proline
    作者:Friedemann,Nora M.; Eustergerling,Astrid; Nubbemeyer,Udo
    参考文献:European Journal Of Organic Chemistry 日期:2012 卷标:2012(4) 页码:837-843]

    51-35-4 = 95687-41-5
    反应条件:1.1 Reagents: Pyridine Solvents: Pyridine; Rt1.2 Reagents: Boron Trifluoride Etherate,Sodium Borohydride Solvents: Tetrahydrofuran; 0 °C; 0 °C -> Rt1.3 Reagents: Methanol; Rt; Rt -> Reflux; > 1 H,Reflux
    标题:Synthesis Of 2-Methyl-2,5-Diazabicyclo[2.2.1]Heptane,Side Chain To Danofloxacin
    作者:Braish,Tamim F.
    参考文献:Organic Process Research & Development 日期:2009 卷标:13(2) 页码:336-340]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; 0 °C; 12 H,Rt; Rt -> 0 °C1.2 Reagents: Acetic Acid; 0 °C
    标题:Prolinol-Based Nucleoside Phosphonic Acids: New Isosteric Conformationally Flexible Nucleotide Analogues
    作者:Vanek,Vaclav; Budesinsky,Milos; Rinnova,Marketa; Rosenberg,Ivan
    参考文献:Tetrahedron 日期:2009 卷标:65(4) 页码:862-876]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Borohydride Solvents: Ethanol,Tetrahydrofuran; 30 Min,Cooled; Overnight,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Ph 7.0
    标题:Backbone-Extended Pyrrolidine Peptide Nucleic Acids (Beppna): Design,Synthesis And Dna/rna Binding Studies
    作者:Govindaraju,T.; Kumar,Vaijayanti A.
    参考文献:Chemical Communications (Cambridge 日期:2005 卷标:(4) 页码:495-497]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Borohydride Solvents: Tetrahydrofuran; 0.5 H,0 °C; 0 °C -> Rt; 2 H,Rt
    标题:Linker Length Modulates Dna Cross-Linking Reactivity And Cytotoxic Potency Of C8/c8' Ether-Linked C2-Exo-Unsaturated Pyrrolo[2,1-C][1,4]Benzodiazepine (Pbd) Dimers
    作者:Gregson,Stephen J.; Howard,Philip W.; Gullick,Darren R.; Hamaguchi,Anzu; Corcoran,Kathryn E.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2004 卷标:47(5) 页码:1161-1174]

    64187-48-0 = 95687-41-5
    反应条件:1.1 Reagents: Lithium Borohydride Solvents: Tetrahydrofuran
    标题:Oligonucleotide Analogs With 4-Hydroxy-N-Acetylprolinol As Sugar Substitute
    作者:Ceulemans,Griet; Van Aerschot,Arthur; Wroblowski,Berthold; Rozenski,Jef; Hendrix,Chris; Et Al
    参考文献:Chemistry - A European Journal 日期:1997 卷标:3(12) 页码:1997-2010]

    = 95687-41-5 [标题:Reaction Conditions
    标题:An Enantioselective Synthesis Of (+)-Crotanecine
    作者:Yadav,Veejendra Kumar; Rueger,Heinrich; Benn,Michael
    参考文献:Heterocycles 日期:1984 卷标:22(12) 页码:2735-8
📜L-羟基脯氨酸置于sodium Tetrahydroborate,氯化亚砜,水,Lithium Chloride,Sodium Hydroxide体系中,用 四氢呋喃,甲基叔丁基醚,水 作为反应溶剂,化学反应 14.5H,反应生成 Cbz-反式-4-羟基-L-脯氨醇
参考文献:新型杂化分子吡咯并苯二氮卓-蒽羧酰亚胺作为抗体-药物偶联物有效载荷的设计,合成和生物评价
标题:新型杂化分子吡咯并苯二氮卓-蒽羧酰亚胺作为抗体-药物偶联物有效载荷的设计,合成和生物评价
摘要:设计,合成了一系列结合吡咯并苯二氮卓 (Pbd) 和蒽羧酰亚胺药效团的新型混合分子,并测试了其对各种癌细胞系的体外细胞毒性.该系列中最有效的化合物37B3表现出亚纳摩尔水平的细胞毒性,Ic 50为 0.17-0.94 Nm.37B3诱导 Dna 损伤并导致肿瘤细胞周期停滞和细胞凋亡.我们使用37B3作为有效载荷与曲妥珠单抗偶联以获得抗体-药物偶联物 (Adc) T-Pba.t-Pba保持了曲妥珠单抗的靶向模式和内化能力.我们证明了 T-Pba 可以通过溶酶体途径降解以释放有效载荷37B3内化后.t-Pba在体外对 Her2 阳性癌细胞显示出强大的杀伤作用.此外,T-Pba 显着抑制胃癌和卵巢癌异种移植小鼠模型中的肿瘤生长,而没有明显的毒性.总的来说,这些研究表明 T-Pba 代表了一种有前途的新 Adc,值得进一步研究.
DOI:10.1021/acs.Jmedchem.2C00471

海关参考信息

专利信息


专利号:US-5419966-A
优先权日:1991-06-10
标 题 :Solid support for synthesis of 3'-tailed oligonucleotides
发明人：REED MICHAEL W; MEYER JR RICH B; PETRIE CHARLES R; TABONE JOHN C
权利人:MICROPROBE CORP
摘要:A solid support for oligonucleotide synthesis has the structure where CPG represents a controlled pore glass matrix, the wavy line represents a carbon chain covalently linking the NH group with the controlled pore glass matrix, X is 2,2'-dimethoxytrityl or H, and R is alkyl, aryl, arylalkyl, heteroalkyl, or heteroaryl. The dimethoxytrityl group is removed from the solid support by treatment with acid, and the oligonucleotide is built, step-by-step in a conventional synthesizer after attachment of the 3' end of the first oligonucleotide unit to the hydroxyl function connected to the R group.

专利号:JP-3256539-B2
优先权日:1990-08-28
标 题:Solid support synthesis of 3'-tailed oligonucleotides via linking molecules

专利号:US-2009203132-A1
优先权日:2004-09-09
标题:Pyrrolidinyl groups for attaching conjugates to oligomeric compounds
发明人：SWAYZE ERIC E; ROBINSON JR DALE E; JEFFERSON ELIZABETH ANNE; DANDE PRASAD; PRAKASH THAZHA P; ALLERSON CHARLES; BHAT BALKRISHEN
权利人:SWAYZE ERIC E; ROBINSON JR DALE E; JEFFERSON ELIZABETH ANNE; DANDE PRASAD; PRAKASH THAZHA P; ALLERSON CHARLES; BHAT BALKRISHEN
摘要:The present invention provides pyrrolidinyl compounds that are useful for preparing conjugated oligomeric compounds. The conjugated pyrrolidinyl compounds can be attached to support medium and provide a free hydroxyl for oligomer synthesis to prepare an oligmeric compound having a 3′-conjugate. Alternatively, the pyrrolidinyl compound can be prepared as a phosphoramidite which can be placed internally or at the 5′-position of an oligomeric compound. These two strategies can be used together to prepare oligomeric compounds having 2 or more conjugates at any selected positions. The present invention also provides methods for modulating gene expression using the conjugated oligomeric compounds.

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