tert-butyl N-(tert-butoxycarbonyl)-D-tyrosinate | 1414025-67-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N-(tert-butoxycarbonyl)-D-tyrosinate
• 英文别名: tert-butyl (tert-butoxycarbonyl)-D-tyrosinate；N-Boc-D-tyrosine tert-butyl ester；tert-butyl (2R)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1414025-67-4
• 化学式: C₁₈H₂₇NO₅
• 分子量: 337.416
• InChiKey: WGJGINMQCMATNP-CQSZACIVSA-N

物化性质

• 沸点：
  476.0±40.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(tert-butoxycarbonyl)-D-tyrosinate 在 N,N'-羰基二咪唑 、 咪唑 、 盐酸羟胺 作用下， 以 乙腈 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Specificity of extended O-aryloxycarbonyl hydroxamates as inhibitors of a class C β-lactamase

  摘要：

  Class C beta-lactamases have previously been shown to be efficiently inactivated by O-aryloxycarbonyl hydroxamates. O-Phenoxycarbonyl-N-benzyloxycarbonylhydroxylamine (1) and O-phenoxycarbonyl-N-(R)-[(4-amino4- carboxy-1-butyl) oxycarbonyl] hydroxylamine (2), for example, were found to be effective inactivators. The present paper describes a structure-activity study of these molecules to better define the important structural elements for high inhibitory activity. The results show that a well-positioned hydrophobic element (which may interact with the Tyr221 residue of the enzyme) and a negatively charged element, e. g. a carboxylate group (which may interact with Arg204), are required for high reactivity with the enzyme. The new compounds were found to inactivate by forming a carbonyl cross-linked enzyme (probably Ser64OCONHLys 315) as for 1 rather than the inert hydroxamoyl derivative observed with 2.

  DOI：

  10.1016/j.bmc.2019.02.023
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 D-tyrosine t-butylester 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以95%的产率得到tert-butyl N-(tert-butoxycarbonyl)-D-tyrosinate
  参考文献：
  名称：

  New precursors for direct radiosynthesis of protected derivatives of O-([18F]Fluoromethyl) tyrosine

  摘要：

  该发明描述了一种新颖且稳定的前体，用于直接放射合成O-([18F]氟甲基)酪氨酸的保护衍生物，并提供了获得这些化合物的方法。

  公开号：

  EP2540710A1

文献信息

• HPLC-free <i>in situ</i>¹⁸F-fluoromethylation of bioactive molecules by azidation and MTBD scavenging
  作者：Yingqing Lu、Ji Young Choi、Sang Eun Kim、Byung Chul Lee

  DOI：10.1039/c9cc04901k

  日期：——

  Sequential usage of azide and MTBD, which generates pure [¹⁸F]fluoromethyl tosylate and scavenges unreacted desmethyl precursors, provided an efficient HPLC-free strategy for the radio-synthesis of ¹⁸F-fluoromethylated compounds.

  使用叠氮和MTBD的顺序使用，生成纯[18F]氟甲基对甲苯磺酰基，并清除未反应的去甲基前体，为18F-氟甲基化合物的无HPLC合成提供了高效策略。
• METHOD FOR PREPARING FLUORINE-18-LABELED FLUOROMETHYL-SUBSTITUTED RADIOPHARMACEUTICALS USING SELECTIVE AZIDE SUBSTITUTION REACTION AND PRECURSOR SCAVENGING
  申请人：Bik Therapeutics Inc.

  公开号：US20210205482A1

  公开（公告）日：2021-07-08

  A method for preparing a fluorine-18-labeled fluoromethyl-substituted radiopharmaceutical using a selective azide substitution reaction includes (1) obtaining a [ 18 F]fluoride from a cyclotron through an 18 O(p,n) 18 F reaction; (2) separating the [ 18 F] fluoride using an acetonitrile reaction solution containing dissolved K 2,2,2 and K 2 CO 3 to obtain a [ 18 F]F − /H 2 18 O solution; (3) heating the [ 18 F]F − /H 2 18 O solution to obtain K 2,2,2 /K 18 F; (4) placing the K 2,2,2 /K 18 F along with a bis(tosyloxy)methane compound into a reactor and adding a reaction solvent to cause a reaction and obtain a first precursor solution; (5) cooling the first precursor solution and adding an azide reagent to cause an azide substitution reaction and obtain a [ 18 F]fluoromethyltosylate compound; (6) adding a bioactive molecule to the [ 18 F]fluoromethyltosylate compound to cause an alkylation reaction and obtain a second precursor solution; and (7) adding a precursor scavenger to the second precursor solution and scavenging unreacted precursors to produce a fluorine-18-labeled fluoromethyl-substituted radiopharmaceutical.

  一种制备氟-18标记的氟甲基取代放射性药物的方法包括：（1）通过选择性叠氮取代反应从超导环中获得[18F]氟化物；（2）使用含有溶解的K2,2,2和K2CO3的乙腈反应溶液分离[18F]氟化物，以获得[18F]F−/H218O溶液；（3）加热[18F]F−/H218O溶液以获得K2,2,2/K18F；（4）将K2,2,2/K18F与双对甲苯磺酰氧基甲烷化合物放入反应器中，并加入反应溶剂引起反应，获得第一前体溶液；（5）冷却第一前体溶液，并加入叠氮试剂引起叠氮取代反应，获得[18F]氟甲基对甲苯磺酸酯化合物；（6）将生物活性分子加入[18F]氟甲基对甲苯磺酸酯化合物中引起烷基化反应，获得第二前体溶液；（7）向第二前体溶液中加入前体清除剂，并清除未反应的前体，以制备氟-18标记的氟甲基取代放射性药物。
• A fast and practical synthesis of tert-butyl esters from 2-tert-butoxypyridine using boron trifluoride·diethyl etherate under mild conditions
  作者：Minh Thanh La、Hee-Kwon Kim

  DOI：10.1016/j.tet.2018.05.050

  日期：2018.7

  A practical direct preparation of tert-butyl esters from 2-tert-butoxypyridine has been developed. This system features the use of boron trifluoride·diethyl etherate in toluene solvent to rapidly achieve the reaction at room temperature. Using this reaction protocol, a variety of tert-butyl esters were synthesized from several different carboxylic acids at high yields. This practical procedure provides

  已经开发了从2-叔丁氧基吡啶实际直接制备叔丁酯的方法。该系统的特点是在甲苯溶剂中使用三氟化硼·乙醚乙醚，可在室温下快速完成反应。使用该反应方案，由几种不同的羧酸以高收率合成了多种叔丁酯。该实用方法为保护具有叔丁基的羧酸提供了一种有前途和有效的方法。
• [EN] DIRECT SYNTHESIS OF 18F-FLUOROMETHOXY COMPOUNDS FOR PET IMAGING AND THE PROVISION OF NEW PRECURSORS FOR DIRECT RADIOSYNTHESIS OF PROTECTED DERIVATIVES OF O-([18F]FLUOROMETHYL) TYROSINE<br/>[FR] SYNTHÈSE DIRECTE DE COMPOSÉS DE 18F-FLUOROMÉTHOXY POUR L'IMAGERIE TEP ET UTILISATION DE NOUVEAUX PRÉCURSEURS POUR LA RADIOSYNTHÈSE DIRECTE DE DÉRIVÉS PROTÉGÉS DE O-([18F]FLUOROMÉTHYL)TYROSINE
  申请人：PIRAMAL IMAGING SA

  公开号：WO2013001088A1

  公开（公告）日：2013-01-03

  The invention describes novel direct synthesis methods for converting a precursor into a PET-tracer with a 18F-fluoromethoxy-group. The invention is also directed to novel and stable precursors for the direct radiosynthesis of protected derivatives of O- ([18F]Fluoromethyl) tyrosines.

  该发明描述了一种新颖的直接合成方法，将前体转化为带有18F-氟甲氧基团的PET示踪剂。该发明还针对直接放射合成O-([18F]氟甲基)酪氨酸保护衍生物的新颖稳定前体。
• DIRECT SYNTHESIS OF 18F-FLUOROMETHOXY COMPOUNDS FOR PET IMAGING AND THE PROVISION OF NEW PRECURSORS FOR DIRECT RADIOSYNTHESIS OF PROTECTED DERIVATIVES OF O-([18F] FLUOROMETHYL) TYROSINE
  申请人：Brumby Thomas

  公开号：US20140309424A1

  公开（公告）日：2014-10-16

  The invention describes novel direct synthesis methods for converting a precursor into a PET-tracer with a 18 F-fluoromethoxy-group. The invention is also directed to novel and stable precursors for the direct radiosynthesis of protected derivatives of O—([ 18 F]Fluoromethyl)tyrosines.

  该发明描述了一种新颖的直接合成方法，将前体转化为具有18F-氟甲氧基团的PET示踪剂。该发明还针对一种新颖且稳定的前体，用于直接放射合成O-([18F]氟甲基)酪氨酸的保护衍生物。