(R)-4-氨基-2-((叔丁氧羰基)氨基)-4-氧桥丁酸甲酯 | 124842-28-0

• 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
• 中文名称: (R)-4-氨基-2-((叔丁氧羰基)氨基)-4-氧桥丁酸甲酯
• 英文名称: L-t-Boc-Asn methyl ester
• 英文别名: N^α-(tert-butoxycarbonyl)-(S)-asparagine methyl ester；BOC-L-asparagine methyl ester；Boc-Asn-OMe；methyl (S)-4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate；N-α-(t-butoxycarbonyl)-L-asparagine methyl ester；methyl (tert-butoxycarbonyl)-L-asparaginate；Boc-Asn-OCH₃；(S)-Methyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate；methyl (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 124842-28-0
• 化学式: C₁₀H₁₈N₂O₅
• 分子量: 246.263
• InChiKey: WBCWYEJCFYVRMG-LURJTMIESA-N

物化性质

• 沸点：
  447.2±40.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  (R)-4-氨基-2-((叔丁氧羰基)氨基)-4-氧桥丁酸甲酯 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 methyl (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-sulfanylidenebutanoate
  参考文献：
  名称：

  The design and synthesis of thrombin inhibitors: analogues of MD805 containing non-polar surrogates for arginine at the P1 position

  摘要：

  A series of monocyclic and bicyclic amino acids have been synthesised and incorporated into thrombin inhibitors based on CGH728, an analogue of the Mitsubishi compound MD805. Benzthiazolylalanine (Bta) was found to be a good non-polar substitute for arginine at the P1 position, yielding compounds with low nanomolar potency and good selectivity for thrombin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00282-1
• 作为产物：
  描述：

  甲醇 、 BOC-L-天冬酰胺 在 ammonium cerium(IV) nitrate 作用下， 以77%的产率得到(R)-4-氨基-2-((叔丁氧羰基)氨基)-4-氧桥丁酸甲酯
  参考文献：
  名称：

  Ceric ammonium nitrate (CAN) mediated esterification of N-Boc amino acids allows either retention or removal of the N-Boc group

  摘要：

  Reaction of N-Boc amino acids with ceric ammonium nitrate in an alcohol as the solvent at room temperature resulted in the esterification of N-Boc amino acids with Boc group retention. When the reaction was conducted at reflux temperature, esterification was accompanied with simultaneous removal of the Boc group. Both reactions gave the desired products in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.136

文献信息

• C-Glycoside Analogues ofN4-(2-Acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine: Synthesis and conformational analysis of a cyclicC-glycopeptide
  作者：Matthias Hoffmann、Fred Burkhart、Gerhard Hessler、Horst Kessler

  DOI：10.1002/hlca.19960790602

  日期：1996.9.18

  propanoic acid (22) can be used in solid-phase peptide synthesis. The conformation of 24 was determined by NMR and molecular-dynamics (MD) techniques. Evidence is provided that the CGaa side chain interacts with the peptide backbone. The different C-glycosylated amino acids 15–21 were prepared by coupling 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-heptonic acid (4) with diamino-acid

  的合成Ç糖苷类似物15-22的ñ 4 - （2-乙酰氨基-2-脱氧- β-d-D-吡喃葡萄糖基）-L-天冬酰胺（ASN（Ñ 4的GlcNAc））具有相反的酰胺键为电子等排取代给出了N-糖苷键的结构。制备了肽环（-D-Pro-Phe-Ala-CGaa-Phe-Phe-）（CGaa = C-糖基化氨基酸；24），以证明3-[（3-acetamido-2,6-anhydro- 4,5,7-三-O-苄基-3-脱氧-β-D-甘油-D-邻庚基庚酰基）氨基] -2-[（9 H-氟-9-酰氧基羰基）氨基]丙酸（22）可以用于固相肽合成。的构象通过NMR和分子动力学（MD）技术确定24。提供的证据表明，CGaa侧链与肽主链相互作用。不同Ç -glycosylated氨基酸15-21被偶合制备3-乙酰氨基-2,6-脱水-4,5,7-三ö苄基-3-脱氧β-D-甘油基-D-庚-带有二氨基酸衍生物8-14的庚酸（4
• [EN] ETHER COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS D'ÉTHER ET LEURS UTILISATIONS
  申请人：BIOTHERYX INC

  公开号：WO2019040274A1

  公开（公告）日：2019-02-28

  The present invention provides compounds that modulate protein function, to restore protein homeostasis and/or cell-cell adhesion. The invention provides methods of modulating protein-mediated diseases, such as cytokine-mediated diseases, disorders, conditions, or responses. Compositions of these compounds are also provided. Methods of treatment, amelioration, or prevention of protein-mediated diseases, disorders, and conditions are also provided.

  本发明提供了调节蛋白功能的化合物，以恢复蛋白稳态和/或细胞间粘附。该发明提供了调节蛋白介导疾病的方法，如细胞因子介导的疾病、紊乱、状况或反应。还提供了这些化合物的组合物。还提供了治疗、改善或预防蛋白介导的疾病、紊乱和状况的方法。
• The Heck reaction with unprotected allylic amidines and guanidines
  作者：Edward C Lawson、William A Kinney、Diane K Luci、Stephen C Yabut、David Wisnoski、Bruce E Maryanoff

  DOI：10.1016/s0040-4039(02)00182-x

  日期：2002.3

  The applicability of Heck methodology to the introduction of unprotected amidines and guanidines was investigated. Unprotected guanidine-substituted olefins were coupled to various simple aryl iodides, and this methodology was then applied to a highly functionalized 6-iodoquinazolinone substrate, providing an efficient synthesis of a new class of vitronectin receptor (αVβ3 integrin) antagonists.

  研究了Heck方法对引入未保护的am和胍的适用性。未受保护的胍基取代烯烃被耦合到各种简单芳基碘，然后这个方法适用于高度官能化6- iodoquinazolinone衬底，提供一类新的玻连蛋白受体的一种高效合成（α V β 3整联）拮抗剂。
• Rotihibins, Novel Plant Growth Regulators from Streptomyces graminofaciens.
  作者：NAOYUKI FUKUCHI、KAZUO FURIHATA、JIRO NAKAYAMA、TOSHINARI Goudo、SEIJI TAKAYAMA、AKIRA ISOGAI、AKINORI SUZUKI

  DOI：10.7164/antibiotics.48.1004

  日期：——

  In the course of screening search for plant growth regulators, a culture filtrate of Streptomyces graminofadens 3C02 was found to inhibit the growth of lettuce seedlings. The active substances, named rotihibin A (1) and B (2), were revealed to be lipo-peptidal compounds. Rotihibins inhibit growth of various plants at below 1 μg/ml, but do not show lethal activity even at higher doses.

  在筛选植物生长调节剂的过程中，发现链霉菌（Streptomyces graminofadens）3C02的培养滤液能够抑制生菜苗的生长。活性物质被命名为rotihibin A (1)和B (2)，被证实为脂肽化合物。Rotihibins在低于1 μg/ml的浓度下抑制多种植物的生长，但即使在更高剂量下也没有表现出致死活性。
• Acceptor-Controlled Transfer Dehydration of Amides to Nitriles
  作者：Hiroyuki Okabe、Asuka Naraoka、Takahiro Isogawa、Shunsuke Oishi、Hiroshi Naka

  DOI：10.1021/acs.orglett.9b01657

  日期：2019.6.21

  dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired

  通过使用二氯乙腈作为水受体，在温和的水性条件下钯催化的伯酰胺脱水有效地进行为腈。设计该转移脱水催化的关键是确定一种有效的水受体二氯乙腈，该水受体在Pd催化剂的帮助下优先于酰胺而不是其他极性官能团反应，并使所需的反应体系趋于能动，从而驱动脱水。