diethyl 2-O-benzyl-L-tartrate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 2-O-benzyl-L-tartrate
• 英文别名: diethyl 2-O-benzyl-(R,R)-tartrate；(2R,3R)-diethyl 2-(benzyloxy)-3-hydroxysuccinate；diethyl (2R,3R)-2-hydroxy-3-phenylmethoxybutanedioate
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: MDMNHGADPKANHJ-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-O-benzyl-L-tartrate 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 2-O-benzyl-3,4-O-isopropylidene-L-threitol
  参考文献：
  名称：

  The first total synthesis of (+)-rogioloxepane A

  摘要：

  The first total synthesis of (+)-rogioloxepane A is described. The alpha,omega -trans-disubstituted oxepene skeleton was stereoselectively constructed via cyclization of the hydroxy epoxide promoted by the (Bu3Sn)(2)O/Zn(OTf)(2) system. The proposed configurations of 6R and 13R were confirmed through this synthetic study. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02281-4
• 作为产物：
  描述：

  diethyl (4R,5R)-2-phenyl-1,3-dioxolane-4,5-dicarboxylate 在 盐酸 、 sodium cyanoborohydride 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 1.0h， 以77%的产率得到diethyl 2-O-benzyl-L-tartrate
  参考文献：
  名称：

  由L（+）-酒石酸合成3α-烷氧基-4β-取代的-2-氮杂环丁酮。

  摘要：

  酒石酸，区域选择性皂化，猪肝酯酶，3-甲氧基-2-氮杂环丁酮，N-羟基-2-硫代吡啶酮，自由基脱羧。描述了由L（+）酒石酸合成3α-烷氧基-4β-氮杂环丁烷酮。区域选择性皂化和甲基化以及立体选择性自由基脱羧烷基化是导致光学纯的反式-β-内酰胺的关键步骤。

  DOI：

  10.1016/s0040-4020(01)81921-9

文献信息

• [EN] PIPERIDINYL-SUBSTITUTED LACTAMS AS GPR119 MODULATORS<br/>[FR] LACTAMES À SUBSTITUTION PIPÉRIDINYLE COMME MODULATEURS DE GPR119
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2011146335A1

  公开（公告）日：2011-11-24

  Compounds of Formula (I): and pharmaceutically acceptable salts thereof in which X1, X2, L, R3, R4, R5, R6, R6a, R7, R9, R9a, and n have the meanings given in the specification, are modulators of GPR119 and are useful in the treatment or prevention of diseases such as such as, but not limited to, type 2 diabetes, diabetic complications, symptoms of diabetes, metabolic syndrome, obesity, dyslipidemia, and related conditions.

  式（I）的化合物及其药学上可接受的盐，其中X1、X2、L、R3、R4、R5、R6、R6a、R7、R9、R9a和n的含义如规范中所述，是GPR119的调节剂，并且在治疗或预防诸如但不限于2型糖尿病、糖尿病并发症、糖尿病症状、代谢综合征、肥胖、血脂异常及相关疾病方面具有用处。
• Development of diacyltetrol lipids as activators for the C1 domain of protein kinase C
  作者：Narsimha Mamidi、Sukhamoy Gorai、Rakesh Mukherjee、Debasis Manna

  DOI：10.1039/c2mb05452c

  日期：——

  The protein kinase C (PKC) family of serine/threonine kinases is an attractive drug target for the treatment of cancer and other diseases. Diacylglycerol (DAG), phorbol esters and others act as ligands for the C1 domain of PKC isoforms. Inspection of the crystal structure of the PKCδ C1b subdomain in complex with phorbol-13-O-acetate shows that one carbonyl group and two hydroxyl groups play pivotal roles in recognition of the C1 domain. To understand the importance of two hydroxyl groups of phorbol esters in PKC binding and to develop effective PKC activators, we synthesized DAG like diacyltetrols (DATs) and studied binding affinities with C1b subdomains of PKCδ and PKCθ. DATs, with the stereochemistry of natural DAGs at the sn-2 position, were synthesized from (+)-diethyl L-tartrate in four to seven steps as single isomers. The calculated EC50 values for the short and long chain DATs varied in the range of 3–6 μM. Furthermore, the fluorescence anisotropy values of the proteins were increased in the presence of DATs in a similar manner to that of DAGs. Molecular docking of DATs (1b–4b) with PKCδ C1b showed that the DATs form hydrogen bonds with the polar residues and backbone of the protein, at the same binding site, as that of DAG and phorbol esters. Our findings reveal that DATs represent an attractive group of C1 domain ligands that can be used as research tools or further structurally modified for potential drug development.

  蛋白激酶C (PKC) 家族的丝氨酸/苏氨酸激酶是治疗癌症和其他疾病的一个有吸引力的药物靶点。二酰基甘油 (DAG)、佛尔波酯等作为PKC异构体C1结构域的配体。检查PKCδ C1b亚结构域与佛尔波-13-O-醋酸酯的复合物的晶体结构显示，一个羰基和两个羟基在C1结构域的识别中起着关键作用。为了了解佛尔波酯的两个羟基在PKC结合中的重要性，并开发有效的PKC激动剂，我们合成了类似DAG的二酰基醇 (DATs)，并研究了它们与PKCδ和PKCθ的C1b亚结构域的结合亲和力。具有天然DAG在sn-2位立体化学的DAT，采用(+)-二乙基L-酒石酸酯在四到七个步骤中合成为单一异构体。短链和长链DAT的计算EC50值在3–6 μM范围内变化。此外，在DAT存在的情况下，蛋白质的荧光各向异性值也以类似DAG的方式增加。DAT（1b-4b）与PKCδ C1b的分子对接显示，DAT与极性残基和蛋白质的主链形成氢键，位于与DAG和佛尔波酯相同的结合位点。我们的发现表明，DAT代表一组有吸引力的C1结构域配体，可以作为研究工具或进一步进行结构修饰以开发潜在药物。
• Solvent-free benzylation of polyols by phase-transfer catalysis or supported reagent methods
  作者：Didier Dubreuil、Jeannine Cleophax、André Loupy

  DOI：10.1016/0008-6215(94)90012-4

  日期：1994.1

  Abstract Solvent-free techniques were successfully and efficiently applied under mild conditions to the perbenzylation of methyl α- d -glucopyranoside and methyl 6-bromo(and 6-chloro)-6-deoxy-α- d -glucopyranoside, and to the selective monobenzylation of diethyl (R,R)-tartrate. Selective 2-O- or 3-O-benzylation of methyl 4,6-O-benzylidene-α- d -galactopyranoside, requiring CH2Cl2 as solvent, was observed

  摘要在温和条件下成功，有效地将无溶剂技术应用于甲基α-d-吡喃葡萄糖苷和甲基6-溴（和6-氯）-6-脱氧-α-d-吡喃葡萄糖苷的过苄基化反应以及选择性的单苄基化反应（R，R）-酒石酸二乙酯 根据铵催化剂的性质，观察到需要CH 2 Cl 2作为溶剂的甲基4，6-O-亚苄基-α-d-吡喃半乳糖苷的选择性2-O-或3-O-苄基化。
• Chiral synthesis of 3,4-disubstituted 2-azetidinones from (R,R)-(+)-tartaric acid
  作者：Alice Gateau-Olesker、Jeannine Cléophax、Stephan D. Géro

  DOI：10.1016/s0040-4039(00)83934-9

  日期：1986.1

  A novel route Is described for the enantioselective synthesis of 2-azetidinones 24 and 25 from (R,R)-(+)-tartaric acid. Monomethylation, monobenzylation of 2 and the use of site specific pig liver esterase (PLE) to produce 6 and 7 are the key steps in the sequence.

  描述了从（R，R）-（+）-酒石酸对映体选择性合成2-氮杂环丁酮24和25的新途径。单甲基化，2的单苄基化以及使用位点特异性猪肝酯酶（PLE）产生6和7是序列中的关键步骤。
• Compounds for the treatment of inflammatory disorders
  申请人：Siddiqui Arshad M.

  公开号：US20060178366A1

  公开（公告）日：2006-08-10

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, aggrecanase, ADMP, LpxC, ADAMs, TACE, TNF-α or combinations thereof.

  本发明涉及式（I）的化合物：或其药学上可接受的盐、溶剂或异构体，可用于治疗由MMPs、aggrecanase、ADMP、LpxC、ADAMs、TACE、TNF-α或其组合介导的疾病或病况。