O-benzyl-L-serine methyl ester | 46460-82-6

• 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: O-benzyl-L-serine methyl ester
• 英文别名: (2S)-O-benzylserine methyl ester；O-benzyl-L-serine methyl ester；methyl ester of O-benzylserine；(S)-methyl-O-benzylserinate；H-β(BnO)Ala-OMe；H-Ser(Bzl)-OMe；methyl (2S)-2-amino-3-phenylmethoxypropanoate
• CAS: 46460-82-6；55895-87-9；84907-81-3
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: PCLKHOKTUJSLDD-JTQLQIEISA-N

物化性质

• 沸点：
  330.2±27.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-benzyl-L-serine methyl ester 在 盐酸 、 methyloxirane 作用下， 生成 L-丝氨酸
  参考文献：
  名称：

  Stereospecific synthesis of α-deuteriated α-amino acids: regiospecific deuteriation of chiral 3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazines

  摘要：

  Base-catalysed deuteriation of (3R)- or (3S)-3-isopropyl-2.5-dimethoxy-3,6-dihydropyrazines in refluxing (CH3OH)-H-2-(H2O)-H-2 gives the [6-H-2(2)]-isotopomer in excellent yields without disturbing the stereogenic centre at C-3. These compounds provide convenient and efficient access to a range of (R)- and (S)-alpha-deuteriated alpha-amino acids, including serine, aspartic acid, allylglycine and phenylalanine, via alkylation of the butyllithium generated C-6 anion.

  DOI：

  10.1039/p19950000157
• 作为产物：
  描述：

  (S)-methyl 3-(benzyloxy)-2-(benzyloxycarbonylamino)propanoate 在 palladium on activated charcoal 1,4-环己二烯 、 氢气 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以90%的产率得到O-benzyl-L-serine methyl ester
  参考文献：
  名称：

  Chemoselective deprotection of benzyl esters in the presence of benzyl ethers, benzyloxymethyl ethers and n-benzyl groups by catalytic transfer hydrogenation

  摘要：

  -COOBn, -PO(OH)OBn, -O-CBz and -N-CBz groups are efficiently and chemoselectively deprotected in the presence of Bn and BOM ethers and N-Bn groups by hydrogenolysis under catalytic transfer hydrogenation using 10 % palladium on carbon as the catalyst and cyclohexadiene as the hydrogen donor.

  DOI：

  10.1016/s0040-4039(00)74195-5

文献信息

• A microwave enhanced cross-metathesis approach to peptidomimetics
  作者：Thomas Morris、David Sandham、Stephen Caddick

  DOI：10.1039/b700804j

  日期：——

  Functionalization of amino acid C- and N-termini with appropriate olefinic moieties allows for the generation of a peptidomimetic via a stereoselective cross-metathesis.

  用适当的烯烃部分对氨基酸C-和N-末端进行官能化可以通过立体选择性交叉复分解产生拟肽。
• Synthesis of sansalvamide A peptidomimetics: triazole, oxazole, thiazole, and pseudoproline containing compounds
  作者：Melinda R. Davis、Erinprit K. Singh、Hendra Wahyudi、Leslie D. Alexander、Joseph B. Kunicki、Lidia A. Nazarova、Kelly A. Fairweather、Andrew M. Giltrap、Katrina A. Jolliffe、Shelli R. McAlpine

  DOI：10.1016/j.tet.2011.11.089

  日期：2012.1

  heterocycles (triazoles, oxazoles, thiazoles, or pseudoprolines) along the macrocyclic backbone. The syntheses of these derivatives employ several approaches that can be applied to convert a macrocyclic peptide into its peptidomimetic counterpart. These approaches include peptide modifications to generate the alkyne and azide for click chemistry, a serine conversion into an oxazole, a Hantzsch reaction

  与用肽类似物观察到的相比，基于肽模拟物的大环化合物通常具有改进的药代动力学特性。描述了基于活性 sansalvamide A 结构的 13 种拟肽衍生物的合成，其中这些类似物沿大环骨架包含杂环（三唑、恶唑、噻唑或假脯氨酸）。这些衍生物的合成采用了几种可用于将大环肽转化为其拟肽对应物的方法。这些方法包括肽修饰以生成用于点击化学的炔烃和叠氮化物、丝氨酸转化为恶唑、Hantzsch 反应生成噻唑以及保护苏氨酸生成假脯氨酸衍生物。此外，我们展示了两种不同的拟肽部分，三唑和噻唑，
• One-Pot Synthesis of Ureido Peptides and Urea-Tethered Glycosylated Amino Acids Employing Deoxo-Fluor and TMSN3
  作者：V. Sureshbabu、H. Hemantha、G. Chennakrishnareddy、T. Vishwanatha

  DOI：10.1055/s-0028-1087538

  日期：2009.2

  urea-linked peptidomimetics and neoglycopeptides under Curtius rearrangement conditions employing Deoxo-Fluor and TMSN3 is described. The method is efficient and circumvents the isolation of acyl azide and isocyanate intermediates. The rearrangement of the in situ generated acyl azide via the acyl fluoride was carried out under ultrasonication followed by amine capture to insert a urea bond. The protocol

  描述了一种简便的一锅法，用于在使用 Deoxo-Fluor 和 TMSN3 的 Curtius 重排条件下合成尿素连接的肽模拟物和新糖肽。该方法有效并且避免了酰基叠氮化物和异氰酸酯中间体的分离。在超声处理下通过酰氟对原位生成的酰基叠氮化物进行重排，然后进行胺捕获以插入脲键。该方案适用于所有常见的 N-氨基甲酸乙酯保护的氨基酸以及糖 6-酸。© Georg Thieme Verlag 斯图加特。
• Asymmetric nucleophilic substitution of α-bromo amides via dynamic kinetic resolution for the preparation of dipeptide analogues
  作者：Jiyoun Nam、Ji-yeon Chang、Eun-kyoung Shin、Hyun Jung Kim、Yangmee Kim、Soonmin Jang、Yong Sun Park

  DOI：10.1016/j.tet.2004.05.094

  日期：2004.7

  Asymmetric nucleophilic substitution reactions of α-bromo α-aryl acetamides derived from l-amino acids are described. The simple and practical syntheses of dipeptide analogues have been developed with dibenzylamine, TBAI and a base to provide 2a–2n and 4 in 50–98% yields with diastereomeric ratios from 74:26 to >99:1. Mechanistic investigations suggest that α-bromo acetamides are configurationally

  描述了衍生自1-氨基酸的α-溴α-芳基乙酰胺的不对称亲核取代反应。用二苄基胺，TBAI和碱开发了二肽类似物的简单实用合成方法，以50-98％的产率提供2a - 2n和4，非对映体比例为74:26至> 99：1。机理研究表明，α-溴乙酰胺在反应条件下构型不稳定，不对称诱导的主要途径是动态动力学拆分。1b的两个差向异构过渡态的半经验计算发现（αS-epimer是反应更快的差向异构体，形成分子间氢键，促进了胺亲核试剂的传递。
• Lipid derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04737518A1

  公开（公告）日：1988-04-12

  Novel lipid derivatives of the formula ##STR1## [wherein R.sup.1 is alkyl or alkylcarbamoyl; R.sup.2 is hydrogen, hydroxy which may be substituted, amino which may be substituted or cyclic amino; R.sup.3 is a chemical binding or alkylene which may be substituted; R.sup.4 is hydrogen, alkyl or aralkyl; X and Y are independently O, S or an imino group which may be substituted, and when Y is an imino group, Y, together with the imino group represented by X or R.sup.4, may form a ring; and Z is imino or a nitrogen-containing heterocyclic ring which may be substituted] and salts thereof have inhibiting activity on platelet activating factor and are useful as a preventive or therapeutic agent for a variety of circulatory diseases and allergic disorders and also as an antineoplastic agent.

  新型脂质衍生物的化学式如下：[其中R.sup.1为烷基或烷基氨酰；R.sup.2为氢、羟基（可取代）、氨基（可取代）或环氨基；R.sup.3为化学键合或烷基（可取代）；R.sup.4为氢、烷基或芳基烷基；X和Y独立地为O、S或可取代的亚胺基，当Y为亚胺基时，Y与X或R.sup.4代表的亚胺基一起可能形成环；Z为亚胺基或含氮杂环，可取代]及其盐具有对血小板活化因子的抑制活性，并可用作多种循环系统疾病和过敏性疾病的预防或治疗剂，同时也可用作抗肿瘤剂。