(S)-ALPHA羟基异正戊酸叔丁酯 | 3519-30-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-ALPHA羟基异正戊酸叔丁酯
• 英文名称: tert-butyl (S)-2-hydroxy-3-methylbutanoate
• 英文别名: L-α-Hydroxy-isovaleriansaeure-tert-butylester；(S)-tert-butyl 2-hydroxy-3-methylbutanoate；tert-butyl (2S)-2-hydroxy-3-methylbutanoate
• CAS: 3519-30-0
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: XQTIFSCLEWPKCF-ZETCQYMHSA-N

物化性质

• 熔点：
  30-31 °C
• 沸点：
  61-63 °C(Press: 1.8 Torr)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (S)-ALPHA羟基异正戊酸叔丁酯 在 palladium on activated charcoal N-甲基吗啉 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 68.0h， 生成 benzyloxycarbonyl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleric acid
  参考文献：
  名称：

  五氟苯酯偶联在与缬氨霉素有关的环二肽合成中的应用

  摘要：

  研究了许多环状二肽的合成策略，包括基于五氟苯基酯的环化方案。研究了胺保护作为苄氧羰基或叔丁氧羰基衍生物的替代方法，并通过原位氢解释放氨基官能团获得了最佳结果。研究了这些方案相对于靶肽环大小的价值。

  DOI：

  10.1016/0040-4020(95)00962-0
• 作为产物：
  描述：

  L-α-羟基异戊酸 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 (S)-ALPHA羟基异正戊酸叔丁酯
  参考文献：
  名称：

  Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides

  摘要：

  Ab initio calculations (B3LYP/Lan12DZ level of theory) were performed in this study to determine all the structural and catalytic zinc parameters required in order to study MMPs and their complexes with hydroxamate inhibitors by means of the AMBER force field. The parameters thus obtained were used in order to study the docking of some known MMPi (Batimastat, CGS 27023A and. Prinomastat) and our previously described inhibitor a which had shown an inhibitory activity for MMP-1, and -2, with the aim of explaining the different selectivity. On this basis the two enantiomers (R)-b and (S)-b were designed and synthesized, as more potent MMP-2 inhibitors than our previously described inhibitor a. Between these two enantiomers the eutomer (R)-b proved to be 24.7 times and 15.3 times more potent than CGS 27023A and the parent compound a on MMP-2, maintaining a higher index of MMP-2/MMP-1 selectivity compared with CGS 27023A and the more potent inhibitor Prinomastat. The hydroxamate (R)-b can be considered as a progenitor of a new class of biphenylsulfonamido-based inhibitors that differ from compound a in the presence of an alkyl side chain on the C alpha atom, and show different potency and selectivity profiles on the two MMPs considered. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.056

文献信息

• Synthesis of novel potassium selective valinomycins
  作者：Janet R. Dawson、Yves L. Dory、John M. Mellor、Jerome F. McAleer

  DOI：10.1016/0040-4020(95)00963-9

  日期：1996.1

  The synthesis is described of three aryl substituted valinomycins, in which the aryl groups are placed around the poles of the cyclodepsipeptide. In one synthesis a valinomycin is prepared carrying a pendant hydroxyphenyl residue. In this synthesis the use of the acetate functionality to protect the phenolic site in tyrosine is developed. The spectroscopic and electrochemical evidence indicating the

  描述了三种芳基取代的缬霉素的合成，其中芳基围绕环二肽肽的两极放置。在一种合成中，制备了带有羟基苯基侧基残基的缬霉素。在该合成中，开发了使用乙酸酯官能团来保护酪氨酸中的酚性位点。光谱和电化学证据表明了这种修饰的缬霉素在改进的离子选择电极的设计中的潜在重要性。
• Carbamate caspase inhibitors and uses thereof
  申请人：——

  公开号：US20020028803A1

  公开（公告）日：2002-03-07

  This invention provides caspase inhibitors of formula I: 1 wherein Z is oxygen or sulfur; R 1 is hydrogen, —CHN 2 , R, CH 2 OR, CH 2 SR, or —CH 2 Y; Y is an electronegative leaving group; R 2 is CO 2 H, CH 2 CO 2 H, or esters, amides or isosteres thereof; R 3 is a group capable of fitting into the S2 subsite of a caspase enzyme; R 4 and R 5 are taken together with the intervening nitrogen to form heterocyclic ring and R is as described in the specification. The compounds are effective inhibitors of apoptosis and IL-1&bgr; secretion.

  这项发明提供了化学式I:1的caspase抑制剂，其中Z为氧或硫；R1为氢、—CHN2、R、CH2OR、CH2SR或—CH2Y；Y为电负离去基团；R2为CO2H、CH2CO2H或其酯、酰胺或同分异构体；R3为能够适配到caspase酶的S2位点的基团；R4和R5与介入的氮一起形成杂环，并且R如规范中所述。这些化合物是有效的凋亡和IL-1β分泌抑制剂。
• First Total Synthesis of Neoantimycin
  作者：Hikaru Ogawa、Hideo Iio、Yoshinosuke Usuki

  DOI：10.1246/cl.150509

  日期：2015.9.5

  The first total synthesis of neoantimycin (1), an unusual ring-extended antibiotic of the antimycin class, has been achieved, using intramolecular transesterification for construction of the 15-membered tetralactone core.

  已成功完成新抗麦角菌素（1）的首次全合成，这是一种不寻常的抗麦角菌素类延环抗生素，采用分子内转酯化反应构建了15元环的四内酯核心。
• Potent Arylsulfonamide Inhibitors of Tumor Necrosis Factor-α Converting Enzyme Able to Reduce Activated Leukocyte Cell Adhesion Molecule Shedding in Cancer Cell Models
  作者：Elisa Nuti、Francesca Casalini、Stanislava I. Avramova、Salvatore Santamaria、Marina Fabbi、Silvano Ferrini、Luciana Marinelli、Valeria La Pietra、Vittorio Limongelli、Ettore Novellino、Giovanni Cercignani、Elisabetta Orlandini、Susanna Nencetti、Armando Rossello

  DOI：10.1021/jm901868z

  日期：2010.3.25

  useful target in anticancer therapy. Herein, we report the synthesis and biological evaluation of new ADAM-17 inhibitors containing an arylsulfonamidic scaffold. Among the new potential inhibitors, two very promising compounds 17 and 18 were discovered, with a nanomolar activity for ADAM-17 isolated enzyme. These compounds proved to be also the most potent in inhibiting soluble ALCAM release in cancer

  活化的白细胞粘附分子（ALCAM）在肿瘤生物学和进展中起着重要作用。我们以前的研究表明，ALCAM在上皮性卵巢癌（EOC）细胞表面表达，并通过ADAM-17介导的脱落以可溶形式释放。此过程与EOC细胞的运动性和侵袭性有关，ADAM-17的非特异性抑制剂会降低EOC的细胞运动性和侵袭性。因此，ADAM-17可能代表抗癌治疗的新靶标。在此，我们报告了含有芳基磺酰胺基支架的新型ADAM-17抑制剂的合成和生物学评估。在新的潜在抑制剂中，两种非常有前途的化合物17和18被发现具有ADAM-17分离酶的纳摩尔活性。这些化合物被证明也是抑制癌细胞中可溶性ALCAM释放的最有效剂，对A2774和SKOV3细胞系表现出纳摩尔活性。
• Zinc‐Catalyzed Enantiospecific sp³–sp³ Cross‐Coupling of α‐Hydroxy Ester Triflates with Grignard Reagents
  作者：Christopher Studte、Bernhard Breit

  DOI：10.1002/anie.200800733

  日期：2008.7.7