D -苏氨酸苄酯 | 82679-58-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苏氨酸类衍生物
• 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: D -苏氨酸苄酯
• 中文别名: D-苏氨酸苄酯；D-苏氨酸苯甲酯
• 英文名称: (2R,3S)-threonine benzyl ester
• 英文别名: D-Threonine Benzyl Ester；benzyl (2R,3S)-2-amino-3-hydroxybutanoate
• CAS: 82679-58-1
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: IHRYAQVOEVWURS-WCBMZHEXSA-N

物化性质

• 沸点：
  364.1±27.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D -苏氨酸苄酯 在 三氟化硼乙醚 、 氢溴酸 、 溶剂黄146 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-2-Benzyloxycarbonylamino-5-[(R)-1-((1R,2R)-1-benzyloxycarbonyl-2-methoxy-propylcarbamoyl)-2-benzylsulfanyl-ethylcarbamoyl]-pentanoic acid benzyl ester
  参考文献：
  名称：

  Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer

  摘要：

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00280-4
• 作为产物：
  描述：

  D-苏氨酸 、 苯甲醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 D -苏氨酸苄酯
  参考文献：
  名称：

  Stereoselective Synthesis of Natural and Non-natural Thomsen-nouveau Antigens and Hydrazide Derivatives

  摘要：

  A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to alpha- or beta-anomers in excellent yields (72-96%) and selectivity (similar to 100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.

  DOI：

  10.1021/acs.orglett.5b00512

文献信息

• Studies on the biosynthesis of clavulanic acid. Part 5. Absolute stereochemistry of proclavaminic acid, the monocyclic biosynthetic precursor of clavulanic acid
  作者：Keith H. Baggaley、Stephen W. Elson、Neville H. Nicholson、John T. Sime

  DOI：10.1039/p19900001521

  日期：——

  carried out with enantiomerically pure threonine derivatives to confirm that the formation of the β-lactam moiety did not impair the integrity of the α- and β-chiral centres and that the enzymatic deacylation reaction was capable of resolving the α-centre of an α-amino-β-hydroxy acid. The enantiomeric purity of intermediates was determined using HPLC, 1H NMR spectroscopy utilising the chiral solvating reagents

  通过显示其构成为（2 S，3 R）-5-氨基-3-羟基-2-（2-氧杂氮杂环丁烷-1-基）戊酸的途径合成了普罗维胺酸（1）。合成材料的光谱性质与天然proclavaminic酸的光谱性质相同，并且与天然产物一样，其通过clavaminic acid合酶转化为clavaminic acid（2）。设计了3-羟基鸟氨酸衍生物的有效合成方法，该方法可分离非对映异构体并通过大肠杆菌的酰基转移酶[EC 3.5.1.11]拆分苏式化合物。。随后通过将受保护的3-羟基鸟氨酸迈克尔加到丙烯酸中，然后使用三苯基膦/二-2-吡啶基二硫化物进行闭环，来修饰β-内酰胺环。用对映体纯的苏氨酸衍生物进行模型反应，以确认β-内酰胺部分的形成不会损害α-和β-手性中心的完整性，并且酶促脱酰反应能够解析α-内酰胺基。 α-氨基-β-羟基酸。中间体的对映体纯度使用HPLC，使用手性溶剂化试剂（R）-和（S）-1-（9-蒽基）-2
• Proline–threonine dipeptide as an organocatalyst for the direct asymmetric aldol reaction
  作者：Srivari Chandrasekhar、Kancharla Johny、Chada Raji Reddy

  DOI：10.1016/j.tetasy.2009.06.018

  日期：2009.8

  A new proline-threonine (H-Pro-Thr-OH) dipeptide has been demonstrated as an efficient organocatalyst for a direct asymmetric aldol reaction. It was found that this new peptide-based catalyst efficiently catalyzed the reaction between an aldehyde and acetone to provide beta-hydroxy ketones in good yields with good enantioselectivities. (c) 2009 Elsevier Ltd. All rights reserved.
• BAGGALEY, KEITH H.;ELSON, STEPHEN W.;NICHOLSON, NEVILLE H.;SIME, JOHN T., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 1521-1533
  作者：BAGGALEY, KEITH H.、ELSON, STEPHEN W.、NICHOLSON, NEVILLE H.、SIME, JOHN T.

  DOI：——

  日期：——
• [EN] NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS NMDA ET UTILISATIONS DE CEUX-CI
  申请人：UNIV NORTHWESTERN

  公开号：WO2013063120A2

  公开（公告）日：2013-05-02

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.
• Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer
  作者：Sigthór Pétursson、Jack E Baldwin

  DOI：10.1016/s0040-4020(98)00280-4

  日期：1998.5

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.