Boc-D-谷氨酸-5-苄酯 | 35793-73-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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: Boc-D-谷氨酸-5-苄酯
• 中文别名: 叔丁氧羰基-D-谷氨酸5苄脂；5-苯甲基N-(叔丁氧羰基)-L-谷氨酸酯；BOC-D-谷氨酸5-苄酯；N-叔丁氧羰基-D-谷氨酸-5-苄酯
• 英文名称: N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid
• 英文别名: (R)-5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid；(2R)-5-benzyloxy-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid；Boc-D-Glu(OBzl)-OH；Boc-D-glutamic acid 5-benzyl ester；N-boc-D-glutamic acid 5-benzyl ester；(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-phenylmethoxypentanoic acid
• CAS: 35793-73-8
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: AJDUMMXHVCMISJ-CYBMUJFWSA-N

物化性质

• 熔点：
  69-71 °C
• 比旋光度：
  5.5 º (c=1% in acetic acid)
• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 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：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-D-Glu(OBzl)-OH
Synonyms: Boc-D-glutamic acid 5-benzyl ester

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Boc-D-Glu(OBzl)-OH
CAS number: 35793-73-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C17H23NO6
Molecular weight: 337.4

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  Boc-D-谷氨酸-5-苄酯 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 N-叔丁氧羰基-D-谷氨酸 1-甲酯
  参考文献：
  名称：

  蛋白磷酸酶抑制剂 (-)-Motuporin 的对映选择性合成

  摘要：

  描述了蛋白质磷酸酶抑制剂 motuporin 1a 的高度收敛不对称合成。单个肽片段 [34 + 35 --> 51] 的合成和偶联，然后进行大环化，得到完全保护的 motuporin 前体 33，通过脱水和酯水解将其转化为天然产物。使用不对称巴豆基硅烷键构建方法引入与天然产物相关的八个立体中心中的六个。我们的方法的特点是在构型明确的乙烯基锌中间体 22 和 (E)-乙烯基碘化物 7 之间进行有效的 Pd(0) 催化交叉偶联反应，得到化合物 43，从而构建了三取代的 (E, E)-motuporin 侧链的二烯系统。

  DOI：

  10.1021/ja0206700
• 作为产物：
  描述：

  D-谷氨酸 在 硫酸 作用下， 生成 Boc-D-谷氨酸-5-苄酯
  参考文献：
  名称：

  使用多销方法固相合成穆拉基二肽（MDP）衍生物。

  摘要：

  报道了固相合成穆拉基二肽衍生物的方法。基于此药物筛选方法，可以通过酰化，还原烷基化，磺酰胺形成，尿素形成，N-烷基化，胺加成或组分Ugi反应潜在地合成多样的穆拉基二肽文库。

  DOI：

  10.1016/s0960-894x(00)00241-9

文献信息

• [EN] PRODRUGS OF D-ISOGLUTAMYL-[D/L]-TRYPTOPHAN<br/>[FR] PROMÉDICAMENTS DE D-ISOGLUTAMYL-[D/L]-TRYPTOPHANE
  申请人：APOTEX TECHNOLOGIES INC

  公开号：WO2012129671A1

  公开（公告）日：2012-10-04

  Provided are carboxylic ester derivatives of formula (I), methods of preparing them, and methods for using them. These compounds are prodrugs of D-isoglutamyl-[D/L]-tryptophan. The in vitro bioconversion of some of the prodrugs to the parent drug D-isoglutamyl-D-tryptophan (or thymodepressin) was tested in human hepatocytes and in human blood. In vivo pharmacokinetic studies following oral administration of some of the prodrugs to rats are also reported.

  提供了公式（I）的羧酸酯衍生物，其制备方法以及使用方法。这些化合物是D-异谷氨酰-[D/L]-色氨酸的前药。对一些前药在人类肝细胞和人类血液中转化为母药D-异谷氨酰-D-色氨酸（或胸腺抑制素）的体外生物转化进行了测试。还报告了将一些前药口服给大鼠后的体内药代动力学研究。
• [EN] PRODRUGS OF D-GAMMA-GLUTAMYL-D-TRYPTOPHAN AND D-GAMMA- GLUTAMYL-L-TRYPTOPHAN<br/>[FR] PROMÉDICAMENTS DE D-GAMMA-GLUTAMYL-D-TRYPTOPHANE ET D-GAMMA-GLUTAMYL-L-TRYPTOPHANE
  申请人：APOTEX TECHNOLOGIES INC

  公开号：WO2012129680A1

  公开（公告）日：2012-10-04

  The present invention provides pro-drugs of D-gamma-glutamyl-[D/L] -tryptophan, said pro-drugs are compounds of Formula I or pharmaceutically acceptable salts thereof, wherein G is C1-C8 alkyl or benzyl, T is C1-C8 alkyl or benzyl, and * is a chiral carbon in a (R) or (S) configuration, provided that when * is in the (R) configuration, at least one of G and T is C5-C8 alkyl; and use of compounds of Formula I in a pharmaceutical composition.

  本发明提供D-γ-谷氨酰-[D/L]-色氨酸的前药，所述前药是化合物I的药用可接受盐，其中G为C1-C8烷基或苄基，T为C1-C8烷基或苄基，*为(R)或(S)构型的手性碳，但当*为(R)构型时，至少有一个G和T为C5-C8烷基；以及化合物I在制药组合物中的使用。
• Novel diarylalkene derivatives and novel diarylalkane derivatives
  申请人：AJINOMOTO CO., INC.

  公开号：US20040167118A1

  公开（公告）日：2004-08-26

  The invention relates to a compound represented by the following general formula (1) or its analogue, which selectively inhibit N-type calcium channels or its analogue, and to a method for treating pain etc. comprising the compound represented by the following general formula (1) or its analogue to a patient in need of such treatment: 1 wherein, A represents CH═CH, etc., a, b, c and d represents CH etc., R1, R2, R3, R4, R5 and R6 represents H etc., V—W represents C═C, etc., n represents 0 to 3, Y1 represents O etc., B represents —(CH2)vCHR21 wherein v is 0 to 3, R21 represents H, a lower alkyl group or the like, etc., G represents —CO—, a covalent bond, etc., m is 0 to 6, R7 and R8 represents H, a lower alkyl group, —COR18a, —COOR20 wherein R18a and R20 each represents a lower alkyl group or the like, etc.

  该发明涉及以下一般式（1）或其类似物所代表的化合物，该化合物选择性地抑制N型钙通道或其类似物，并涉及将该一般式（1）或其类似物所代表的化合物用于需要此类治疗的患者的治疗方法： 1 其中，A代表CH═CH等，a、b、c和d代表CH等，R1、R2、R3、R4、R5和R6代表H等，V—W代表C═C等，n代表0至3，Y1代表O等，B代表—(CH2)vCHR21，其中v为0至3，R21代表H、较低的烷基基团或类似物等，G代表—CO—、共价键等，m为0至6，R7和R8代表H、较低的烷基基团、—COR18a、—COOR20，其中R18a和R20各自代表较低的烷基基团或类似物等。
• Facile N-Urethane-Protected α-Amino/Peptide Thioacid Preparation Using EDC and Na2S
  作者：Vommina Sureshbabu、T. Vishwanatha、M. Samarasimhareddy

  DOI：10.1055/s-0031-1290091

  日期：2012.1

  We report herein an efficient protocol for the synthesis of N-urethane-protected α-amino/peptide thioacids from their corresponding acids mediated by EDC and Na2S. The fast reaction under mild conditions enabled the process to be completed in shorter duration with good yield circumventing column purification. The chemistry is compatible with a wide variety of urethane protecting groups, side-chain functionalities, and sterically hindered amino ­acids.

  本文报道了一种高效的方法，通过EDC和Na2S介导，从相应的酸合成N-urethane保护的α-氨基酸/肽硫酸酯。在温和条件下快速反应使得该过程能在较短时间内完成，且产率良好，无需柱层析纯化。该化学方法适用于多种urethane保护基团、侧链功能团以及空间位阻氨基酸。
• Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross‐Linking Activity of a Transpeptidase of <scp>l,d</scp> Specificity
  作者：Saidbakhrom Saidjalolov、Zainab Edoo、Matthieu Fonvielle、Louis Mayer、Laura Iannazzo、Michel Arthur、Mélanie Etheve‐Quelquejeu、Emmanuelle Braud

  DOI：10.1002/chem.202004831

  日期：2021.2.15

  The carbapenem class of β‐lactams has been optimized against Gram‐negative bacteria producing extended‐spectrum β‐lactamases by introducing substituents at position C2. Carbapenems are currently investigated for the treatment of tuberculosis as these drugs are potent covalent inhibitors of l,d‐transpeptidases involved in mycobacterial cell wall assembly. The optimization of carbapenems for inactivation

  碳青霉烯类β-内酰胺类通过针对C2位置引入取代基而针对产生广谱β-内酰胺酶的革兰氏阴性细菌进行了优化。目前正在研究碳青霉烯类药物用于治疗结核病，因为这些药物是l，d的有效共价抑制剂参与分枝杆菌细胞壁组装的转肽酶。本文通过利用C 8羟基的亲核性引入化学多样性来寻找用于灭活这些异常靶标的碳青霉烯类的优化。由于β-内酰胺是肽聚糖前体的结构类似物，因此选择取代基可增加药物和底物之间的相似性。有效地合成了十四个肽-卡宾。由于在位置C2引入苯乙硫基取代基的积极影响，它们比美罗培南参考药物更有效，但在位置C8添加的拟肽不能进一步提高活性。因此，可以修饰位置C8以调节高效碳青霉烯类的药代动力学性质。