D-valine t-butyl ester | 21691-52-1

• 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: D-valine t-butyl ester
• 英文别名: D-Val-O-t-Bu；D-valine tert-butyl ester；H-D-Val-O^tBu；R-(-)-valine t-butyl ester；(R)-tert-Butyl 2-amino-3-methylbutanoate；tert-butyl (2R)-2-amino-3-methylbutanoate
• CAS: 21691-52-1
• 化学式: C₉H₁₉NO₂
• mdl: MFCD21234592
• 分子量: 173.255
• InChiKey: RJBVJBGFJIHJSZ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-valine t-butyl ester 在 TEA 、 二苯基磷酸 作用下， 以 三氟乙酸 为溶剂， 反应 6.0h， 生成 Z-Phe-D-Val-OH
  参考文献：
  名称：

  An extensive survey by the use of high performance liquid chromatography on racemization during the coupling of benzyloxycarbonyl-L-phenylalanyl-L-valine with L-proline tert-butyl ester.

  摘要：

  通过使用高精度的高效液相色谱法，可以方便快捷地确定苄氧羰基-L-苯丙氨酰-L-缬氨酸与L-脯氨酰叔丁酯偶联时的消旋化程度和耦合效率。对各种已知的耦合方法进行了广泛的研究，结果表明，使用二苯基膦酰叠氮（DPPA）和尤其二乙基膦酰氰化物（DEPC）的耦合方法效果最佳。此外，还总结了将DPPA和DEPC作为肽耦合试剂的报告结果（见表I）。

  DOI：

  10.1248/cpb.30.3147
• 作为产物：
  描述：

  D-缬氨酸 在 sodium hydroxide 、 硫酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 D-valine t-butyl ester
  参考文献：
  名称：

  高效（约40克）实验室规模制备（S）-和（R）-缬氨酸叔丁酯

  摘要：

  已经开发了用于制备对映体纯的（S）-和（R）-缬氨酸叔丁酯的大实验室规模（约40g）的方法。该方法包括三个步骤：制备N -TFA-缬氨酸，在硫酸存在下使用2-甲基丙烯在二恶烷中制备缬氨酸叔丁酯，以及分离目标化合物作为乙酸酯衍生物。相对于起始缬氨酸，总产率高达70％，ee大于98％（通过HPLC）。

  DOI：

  10.1016/s0957-4166(02)00532-3
• 作为试剂：
  描述：

  偶氮二甲酸二叔丁酯 、 ethyl 1-methyl-2,5-dioxopyrrolidine-3-carboxylate 在 (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide 、 lanthanum(III) nitrate hexahydrate 、 D-valine t-butyl ester 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (+)-di-tert-butyl 1-(3-(ethoxycarbonyl)-1-methyl-2,5-dioxopyrrolidin-3-yl)hydrazine-1,2-dicarboxylate 、 (+)-di-tert-butyl 1-(3-(ethoxycarbonyl)-1-methyl-2,5-dioxopyrrolidin-3-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Managing Highly Coordinative Substrates in Asymmetric Catalysis: A Catalytic Asymmetric Amination with a Lanthanum-Based Ternary Catalyst

  摘要：

  Full details of a catalytic asymmetric amination with a lanthanum/amide-based ligand catalyst system are described. A catalyst comprising La(NO3)(3)center dot 6H(2)O, (R)-3a and H-D-Val-V'Bu was identified to promote the catalytic asymmetric amination of nonprotected succinimide derivative 1 with as little as 1 mol % catalyst loading Mechanistic studies by various spectroscopic analyses and several control and kinetic experiments suggested that the catalyst components were in equilibrium between the associated and dissociated forms, and that the reaction likely proceeded through a La(NO3)(3)center dot 6H(2)O/(R)-3a/H-D-Val-O'Bu ternary complex. This catalyst system was also effective for asymmetric amination of N-nonsubstituted alpha-alkoxycarbonyl amides 7, hitherto unprecedented substrates in asymmetric catalysis, probably due to their attenuated reactivity and difficult stereocontrol, affording the amination products in up to > 99% yield and > 99% ee. The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.

  DOI：

  10.1021/ja9052653

文献信息

• [EN] DIHYDROPYRROLONAPHTYRIDINONE COMPOUNDS AS INHIBITORS OF JAK<br/>[FR] COMPOSÉS DE DIHYDROPYRROLONAPHTYRIDINONE COMME INHIBITEURS DE JAK
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2010144486A1

  公开（公告）日：2010-12-16

  Disclosed are JAK inhibitors of formula (I) where G1, R1, R2, R3, R4, R5, R6, and R7 are defined in the specification. Also disclosed are pharmaceutical compositions, kits and articles of manufacture which contain the compounds, methods and materials for making the compounds, and methods of using the compounds to treat diseases, disorders, and conditions involving the immune system and inflammation, including rheumatoid arthritis, hematological malignancies, epithelial cancers (i.e., carcinomas), and other diseases, disorders or conditions associated with JAK.

  揭示了式(I)的JAK抑制剂，其中G1、R1、R2、R3、R4、R5、R6和R7在规范中定义。还披露了含有这些化合物的药物组合物、试剂盒和制造物品，制备这些化合物的方法和材料，以及使用这些化合物治疗涉及免疫系统和炎症的疾病、紊乱和症状的方法，包括类风湿关节炎、血液恶性肿瘤、上皮癌（即癌症）和其他与JAK相关的疾病、紊乱或症状。
• SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF
  申请人：Alios BioPharma, Inc.

  公开号：US20150105341A1

  公开（公告）日：2015-04-16

  Disclosed herein are nucleosides, nucleotides and nucleotide analogs, methods of synthesizing the same and methods of treating diseases and/or conditions such as a Picornavirus and/or Flaviviridae infection with one or more nucleosides, nucleotides and nucleotide analogs.

  本文披露了核苷、核苷酸和核苷酸类似物，以及它们的合成方法以及利用一个或多个核苷、核苷酸和核苷酸类似物治疗如小核糖核病毒和/或黄病毒科感染等疾病和/或症状的方法。
• Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (−)-Longirabdolactone, and (−)-Effusin
  作者：Jianpeng Zhang、Zijian Li、Junming Zhuo、Yue Cui、Ting Han、Chao Li

  DOI：10.1021/jacs.9b03978

  日期：2019.5.22

  Structurally complex and bioactive ent-kaurane diterpenoids have well-characterized biological functions and have drawn widespread attention from chemists for many decades. However, construction of highly oxidized forms of such diterpenoids still presents considerable challenges to synthetic chemists. Herein, we report the first total syntheses of C19 oxygenated spiro-lactone ent-kauranoids, including

  结构复杂且具有生物活性的 ent-kaurane 二萜类化合物具有良好的生物学功能，几十年来一直受到化学家的广泛关注。然而，构建此类二萜类化合物的高度氧化形式仍然对合成化学家提出了相当大的挑战。在此，我们报告了 C19 含氧螺内酯 ent-kauranoids 的首次全合成，包括 longirabdiol、longirabdolactone 和 effusin。通过三个基于自由基的反应实现了用于所有三种合成的通用中间体的简明合成：（1）新设计的串联脱羧环化/烯基化序列，该序列与邻位烯基化同时形成顺式 19，6-内酯， (2) Ni催化的脱羧Giese反应，立体选择性地构建C10季铵，(3) 乙烯基自由基环化产生刚性双环[3.2.1]辛烷。来自共同中间体的一系列后期氧化依次提供每种天然产物。对这些合成天然产物的进一步生物学评估揭示了广泛的抗癌活性。
• [EN] DIPHENYLAZETIDINONE DERIVATES PROCESSING CHOLESTEROL ABSORPTION INHIBITORY ACTIVITY<br/>[FR] DERIVES DIPHENYLAZETIDINONE PRESENTANT UNE ACTIVITE D'INHIBITION D'ABSORPTION DU CHOLESTEROL
  申请人：ASTRAZENECA AB

  公开号：WO2005061451A1

  公开（公告）日：2005-07-07

  Compounds of formula (XV): [Chemical formula should be inserted here. Please see paper copy] (XV) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.

  公式（XV）的化合物：[应在此处插入化学公式。请参见纸质副本]（XV）（其中变量组如内部定义）药物可接受的盐、溶剂化物、这些盐的溶剂化物和前药及其用作治疗高脂血症的胆固醇吸收抑制剂。还描述了它们的制造过程和含有它们的药物组合物。
• Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol
  作者：Fangyu Du、Qifan Zhou、Yang Fu、Yuanguang Chen、Ying Wu、Guoliang Chen

  DOI：10.1055/s-0039-1690707

  日期：2019.12

  Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C–N coupling reactions proceed under mild conditions and exhibit good functional group tolerance

  在本文中，我们报告了天然配体 quebrachitol (QCT) 作为 Cu(II) 催化剂的促进剂，它对各种胺和相关芳基卤化物的 N-芳基化非常有效。通过使用二甘醇（DEG）作为配体和溶剂，以高收率获得了一系列二芳胺衍生物。C-N偶联反应在温和的条件下进行并表现出良好的官能团耐受性。