(S)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯 | 108149-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (S)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯
• 中文别名: (S)-4-羟甲基-2,2-二甲基恶唑烷-3-甲酸叔丁基酯；(S)-4-羟甲基-2,2-二甲基恶唑烷-3-羧酸叔丁酯
• 英文名称: tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: (S)-tert-butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate；tert-butyl (S)-4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate；(S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 108149-65-1
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: DWFOEHLGMZJBAA-QMMMGPOBSA-N

物化性质

• 熔点：
  36 °C
• 沸点：
  314.1±27.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-1-Boc-2,2-dimethyl-4-hydroxymethyl-oxazolidine
Synonyms:

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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: (S)-1-Boc-2,2-dimethyl-4-hydroxymethyl-oxazolidine
CAS number: 108149-65-1

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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: C11H21NO4
Molecular weight: 231.3

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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

制备方法与用途

超分子主体材料

反应信息

• 作为反应物：
  描述：

  (S)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯 在 草酰氯 、 四丁基碘化铵 、 potassium carbonate 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.66h， 生成 (4R)-4-(2-ethoxycarbonyl-vinyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  立体异构路线到四个立体异构体3'-乙酰氧基环戊烯基甘氨酸衍生物

  摘要：

  已经开发了从1-丝氨酸到四种立体异构体3'-乙酰氧基环戊烯基甘氨酸衍生物的短而有效的合成途径。该方法以立体选择性共轭加成和闭环复分解为关键步骤。 氨基酸-手性库-易位-迈克尔加成-立体选择性合成

  DOI：

  10.1055/s-0031-1289645
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 24.5h， 生成 (S)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯
  参考文献：
  名称：

  具有较长手性取代基的烟碱乙酰胆碱受体和硝基亚甲基新烟碱衍生物的对接模型及其生物学活性

  摘要：

  在本研究中，合成具有在咪唑烷环上第5位含有硫原子，氧原子或芳香环的取代基的硝基亚甲基新烟碱衍生物，以评估其对烟碱乙酰胆碱受体（nAChR）的亲和力及其对成年雌性家蝇的杀虫活性。 。将烷基化衍生物的受体亲和力与具有醚或硫醚基团的化合物的受体亲和力进行比较后发现，碳原子向硫原子的转化不会影响受体亲和力，而向氧原子的转化则对受体亲和力不利。 。具有苄基或苯基的化合物的受体亲和力低于未取代的化合物。连接在咪唑烷环上第5位的正丁基。对nAChR-配体模型的对接研究表明，通过掠过形成结合区的氨基酸，配体结合区会随着取代基长度的增加而扩展。通过考虑log P和取代基中杂原子（包括硫和氧原子）的数量，化合物的杀虫活性与受体亲和力呈正相关 ，这表明杀虫活性受受体亲和力，疏水性和代谢稳定性的影响的化合物。

  DOI：

  10.1016/j.bmc.2014.12.058

文献信息

• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2018149419A1

  公开（公告）日：2018-08-23

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。
• Asymmetric Total Synthesis of (+)-Didemniserinolipid B via Achmatowicz Rearrangement/Bicycloketalization
  作者：Jingyun Ren、Rongbiao Tong

  DOI：10.1021/jo501142q

  日期：2014.8.1

  of (+)-didemniserinolipid B in 19 linear steps, featuring a highly efficient and enantioselective construction of 6,8-dioxabicyclo[3.2.1]octane (6,8-DOBCO) framework via a rarely explored Achmatowicz rearrangement/bicycloketalization strategy. In addition, the first total synthesis of the proposed (+)-didemniserinolipid C was accomplished with 41.6% yield in 4 steps from a common advanced intermediate

  开发了一种新的合成策略，以19个线性步骤不对称地合成（+）-二酰胺二脂B，具有高效，对映选择性的6,8-二氧杂双环[3.2.1]辛烷（6,8-DOBCO）构架通过很少探索的Achmatowicz重排/双环缩酮化策略。另外，提出的（+）-二去脂神经节苷脂C的第一个全合成反应是从一个普通的高级中间体18分四步以41.6％的收率完成的，并且提出了一种可能的（+）-二去脂神经节苷脂C的修正结构。新的聚合合成策略极大地加快了双双神经油脂及其类似物进入生物活性评估的进程。
• New Antibiotic Candidates against <i>Helicobacter pylori</i>
  作者：Shanzhi Wang、Scott A. Cameron、Keith Clinch、Gary B. Evans、Zhimeng Wu、Vern L. Schramm、Peter C. Tyler

  DOI：10.1021/jacs.5b06110

  日期：2015.11.18

  consequence, 10 new H. pylori antibiotic candidates are identified, all of which prevent H. pylori growth at concentrations 16-2000-fold lower than the five antibiotics, amoxicillin, metronidazole, levofloxacin, tetracyclin, and clarithromycin, commonly used to treat H. pylori infections. X-ray crystal structures of MTAN cocrystallized with several inhibitors show them to bind in the active site making interactions

  幽门螺杆菌是一种革兰氏阴性细菌，定植于世界 50% 以上人口的肠道中。它是大多数消化性溃疡的原因，也是胃癌的重要危险因素。幽门螺杆菌感染的抗生素治疗具有挑战性，因为耐药性已经发展到具有传统作用机制的抗生素。幽门螺杆菌使用一种不寻常的途径进行甲基萘醌生物合成，其中一个重要步骤是由 5'-甲硫腺苷/S-腺苷高半胱氨酸核苷酶 (MTAN) 催化。我们用该酶的过渡态类似物验证了 MTAN 作为靶标的作用 [Wang, S.; 哈帕莱宁，AM；严，F。等人。生物化学 2012, 51, 6892-6894]. 只有当 MTAN 抑制剂既能与 MTAN 靶标紧密结合，又能穿透革兰氏阴性幽门螺杆菌中的复杂细胞膜时，MTAN 抑制剂才会成为有用的候选药物。在这里，我们探索用于抑制 MTAN 和抑制培养的幽门螺杆菌生长的结构支架。这里报告的 16 个类似物是幽门螺杆菌 MTAN 的过渡态类似物，解离常数为 50
• [EN] TREATMENT OF H. PYLORI INFECTIONS USING MTAN INHIBITORS<br/>[FR] TRAITEMENT D'INFECTIONS DUES À H PYLORI À L'AIDE D'INHIBITEURS DE LA MTAN
  申请人：EINSTEIN COLL MED

  公开号：WO2015123101A1

  公开（公告）日：2015-08-20

  Methods of treating infections due to Helicobacter pylori (H. pylori), in particular in subjects having a peptic ulcer, are disclosed where the methods comprise administering inhibitors of H. pylori MTAN (5'-methylthioadenosine nucleosidase) to the subject.

  治疗幽门螺杆菌（H. pylori）感染的方法，特别是针对患有消化性溃疡的患者，包括向患者施用H. pylori MTAN（5'-甲硫腺苷核苷酸酶）抑制剂的方法。
• [EN] PHOSPHORIBOSYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE PHOSPHORIBOSYLTRANSFÉRASES ET LEURS UTILISATIONS
  申请人：IND RES LTD

  公开号：WO2012150866A1

  公开（公告）日：2012-11-08

  The invention relates to compounds of formula (I) that are inhibitors of hypoxanthine and/or guanine purine phosphoribosyltransferases and to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and methods of treating diseases or conditions in which it is desirable to inhibit hypoxanthine and/or guanine purine phosphoribosyltransferases. Such diseases include malaria.

  这项发明涉及到式（I）的化合物，这些化合物是次黄嘌呤和/或鸟嘌呤磷酸核糖转移酶的抑制剂，以及含有这些化合物的药物组合物、制备这些化合物的方法，以及治疗希望抑制次黄嘌呤和/或鸟嘌呤磷酸核糖转移酶的疾病或症状的方法。这些疾病包括疟疾。