(R)-2,2-二甲基-恶唑烷-3,4-二甲酸3-叔-丁酯 | 660852-86-8

• 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)-2,2-二甲基-恶唑烷-3,4-二甲酸3-叔-丁酯
• 中文别名: (R)-3-BOC-2,2-二甲基噁唑烷-4-甲酸
• 英文名称: (4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid
• 英文别名: 3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid；(R)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester；2,2-dimethyloxazolidine-(4R)-3,4-dicarboxylic acid 3-tert-butyl ester；(R)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester；(R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid；(R)-3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-carboxylic acid；(R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid；(4R)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidine-4-carboxylic acid
• CAS: 660852-86-8
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: XUYBSTJQGVZMSK-SSDOTTSWSA-N

物化性质

• 沸点：
  358.2±42.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319

反应信息

• 作为反应物：
  描述：

  (R)-2,2-二甲基-恶唑烷-3,4-二甲酸3-叔-丁酯 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (R)-4-乙酰基-2,2-二甲基噁唑烷-3-羧酸叔丁酯
  参考文献：
  名称：

  Effects on polo-like kinase 1 polo-box domain binding affinities of peptides incurred by structural variation at the phosphoamino acid position

  摘要：

  Protein-protein interactions (PPIs) mediated by the polo-box domain (PBD) of polo-like kinase 1 (Plk1) serve important roles in cell proliferation. Critical elements in the high affinity recognition of peptides and proteins by PBD are derived from pThr/pSer-residues in the binding ligands. However, there has been little examination of pThr/pSer mimetics within a PBD context. Our current paper compares the abilities of a variety of amino acid residues and derivatives to serve as pThr/pSer replacements by exploring the role of methyl functionality at the pThr beta-position and by replacing the phosphoryl group by phosphonic acid, sulfonic acid and carboxylic acids. This work sheds new light on structure activity relationships for PBD recognition of phosphoamino acid mimetics. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.05.036
• 作为产物：
  描述：

  (S)-n-boc-3-氨基-4-羟基丁酸 在 三氟化硼乙醚 、 potassium carbonate 、 lithium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.0h， 生成 (R)-2,2-二甲基-恶唑烷-3,4-二甲酸3-叔-丁酯
  参考文献：
  名称：

  Synthesis of a novel series of 2,3,4-trisubstituted oxazolidines designed by isosteric replacement or rigidification of the structure and cytotoxic evaluation

  摘要：

  2,3,4-三取代噁唑啉结构的刚化增强了对LNCaP细胞的活性，而不影响正常细胞增殖。

  DOI：

  10.1039/c4md00136b

文献信息

• Development of Peptidomimetics with a Vinyl Sulfone Warhead as Irreversible Falcipain-2 Inhibitors
  作者：Roberta Ettari、Emanuela Nizi、Maria Emilia Di Francesco、Marie-Adrienne Dude、Gabriele Pradel、Radim Vičík、Tanja Schirmeister、Nicola Micale、Silvana Grasso、Maria Zappalà

  DOI：10.1021/jm701141u

  日期：2008.2.1

  This paper describes the synthesis of a new class of peptidomimetic cysteine protease inhibitors based on a 1,4-benzodiazepine scaffold and on an electrophilic vinyl sulfone moiety. The former was introduced internally to a peptide sequence that mimics the fragment D-Ser-Gly; the latter was built on the P1-P1' site and reacts as a classical "Michael acceptor", leading to an alkylated enzyme by irreversible

  本文介绍了一种新型的拟肽半胱氨酸蛋白酶抑制剂的合成，该抑制剂基于1,4-苯并二氮杂pine骨架和亲电子乙烯基砜部分。前者在内部被引入到模拟片段D-Ser-Gly的肽序列中。后者建立在P1-P1'位点上，并作为经典的“迈克尔受体”反应，通过不可逆地添加活性位点半胱氨酸的硫醇基团生成烷基化酶。乙烯基砜部分的引入已通过烯烃交叉复分解完成，烯烃复分解是形成碳-碳双键的有力工具。新化合物2-3已被证明是有效的和选择性的falcipain-2抑制剂，falcipain-2是一种从恶性疟原虫中分离出来的半胱氨酸蛋白酶，具有抗血浆活性。
• Synthesis of C-glycosyl amino acids: scope and limitations of the tandem Tebbe/Claisen approach
  作者：David J. Chambers、Graham R. Evans、Antony J. Fairbanks

  DOI：10.1016/j.tetasy.2004.11.035

  日期：2005.1

  as substrates for the tandem Tebbe/Claisen approach to the synthesis of C-glycosyl amino acids. Whilst esters of substituted α-amino acids do not successfully undergo Tebbe, or other, methylenation, esters of β- or γ-amino acids are methylenated to yield vinyl ethers, which then undergo smooth thermal rearrangement to yield β-C-glycoside products. tert-Butyl esters are found to be unreactive to the

  氨基酸可用作与3-羟基缩醛酯化的偶联伴侣，作为串联Tebbe / Claisen方法合成C-糖基氨基酸的底物。尽管取代的α-氨基酸的酯未成功进行Tebbe或其他亚甲基化作用，但β-或γ-氨基酸的酯被亚甲基化生成乙烯基醚，然后进行平稳的热重排以生成β- C-糖苷产物。叔丁基酯被发现是不反应的试剂特伯，这样叔丁基保护可被用于其它羧酸。
• [EN] ARYL HETEROBICYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ARYLÉS EN TANT QUE BLOQUEURS DU CANAL POTASSIQUE SHAKER KV1.3
  申请人：DE SHAW RES LLC

  公开号：WO2021071832A1

  公开（公告）日：2021-04-15

  A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is described, where the substituents are as defined herein. Pharmaceutical compositions including the same and method of using the same are also described.

  描述了化合物式(I)或其药用可接受的盐，其中取代基如本文所定义。还描述了包括该化合物的药物组合物以及使用该化合物的方法。
• Novel sphingosine kinase type 1 inhibitors, compositions and processes for using same
  申请人：Zipkin Robert Elliot

  公开号：US20100035959A1

  公开（公告）日：2010-02-11

  Provided are novel compositions which uniquely inhibit sphingosine kinase Type 1 (SphK1) and which are useful in a number of applications including killing or damaging cancer cells, inducing apoptosis, inhibiting growth, metastasis and development of chemoresistance in cancer cells, leukemia, increasing the effectiveness of anti-cancer agents, attenuating immune reactivity, inhibiting survival signaling in cancer cells, and reducing symptoms of multiple sclerosis.

  提供了一种独特抑制鞘氨醇激酶1（SphK1）的新型组合物，可用于许多应用，包括杀灭或损害癌细胞、诱导凋亡、抑制癌细胞生长、转移和化疗耐药性的发展、白血病、增加抗癌药物的有效性、减轻免疫反应、抑制癌细胞的生存信号，并减轻多发性硬化症状。
• [EN] ISOINDOLINE COMPOSITIONS AND METHODS FOR TREATING NEURODEGENERATIVE DISEASE<br/>[FR] COMPOSITIONS ISOINDOLINE ET MÉTHODES DE TRAITEMENT D'UNE MALADIE NEURODÉGÉNÉRATIVE
  申请人：COGNITION THERAPEUTICS INC

  公开号：WO2015116923A1

  公开（公告）日：2015-08-06

  Isoindoline sigma-2 receptor antagonist compounds, pharmaceutical compositions comprising such compounds, and methods for inhibiting Abeta- associated synapse loss or synaptic dysfunction in neuronal cells, modulating an Abeta-associated membrane trafficking change in neuronal cells, and treating cognitive decline associated with Abeta pathology are provided.

  提供Isoindoline sigma-2受体拮抗剂化合物，包括这种化合物的药物组合物，以及用于抑制神经元细胞中Abeta相关突触丢失或突触功能障碍，调节神经元细胞中Abeta相关膜运输变化，以及治疗与Abeta病理相关的认知衰退的方法。