(2R,5R)-5-羟基-1,3-氧硫杂环-2-羧酸 (1R,2S,5R)-5-甲基-2-异丙基环己酯 | 147126-62-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2R,5R)-5-羟基-1,3-氧硫杂环-2-羧酸 (1R,2S,5R)-5-甲基-2-异丙基环己酯
• 中文别名: (2R,5R)-5-羟基-[1,3]-氧硫杂环戊烷-2-羧酸孟酯；(2R,5R)-5-羟基-1,3-氧硫杂环-2-羧酸(1R,2S,5R)-5-甲基-2-异丙基环己酯；(1R,2S,5R)-5-甲基-2-异丙基环己酯；拉米夫定中间体HME；HME
• 英文名称: (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester
• 英文别名: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylate
• CAS: 147126-62-3
• 化学式: C₁₄H₂₄O₄S
• 分子量: 288.408
• InChiKey: KXKDZLRTIFHOHW-CYRBOEJBSA-N

物化性质

• 熔点：
  99-1010C
• 沸点：
  402.3±45.0 °C(Predicted)
• 密度：
  1.16
• LogP：
  3.18
• 解离常数：
  7.36 at 22℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，干燥密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexy
ester
Synonyms: (2R,5R)-5-Hydroxy[1,3]oxathiolane-2-carboxylic Acid L-menthol Ester

---

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: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl
ester
147126-62-3
CAS number:

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H24O4S
Molecular weight: 288.4

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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, sulfur 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

(2R,5R)-5-羟基-1,3-氧硫杂环-2-羧酸 和 (1R,2S,5R)-5-甲基-2-异丙基环己酯 用作研究用途的化合物。

反应信息

• 作为反应物：
  描述：

  (2R,5R)-5-羟基-1,3-氧硫杂环-2-羧酸 (1R,2S,5R)-5-甲基-2-异丙基环己酯 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-氨基-2-氧代-2H-嘧啶-1-基)-[1,3]1,3-氧硫杂环戊-2-甲酸孟酯
  参考文献：
  名称：

  通过动态动力学拆分对拉米夫定（3TC ™）进行实用的对映选择性合成

  摘要：

  描述了拉米夫定1的实用对映选择性合成。5-羟基氧杂硫杂环戊烷的高效动态动力学拆分，然后进行氯化和胞嘧啶的引入，可有效合成拉米夫定。

  DOI：

  10.1016/j.tetlet.2005.10.002
• 作为产物：
  描述：

  (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-mercaptoacetate 在 磺酰氯 、 水 、 碳酸氢钠 作用下， 以 甲苯 为溶剂， 反应 13.34h， 生成 (2R,5R)-5-羟基-1,3-氧硫杂环-2-羧酸 (1R,2S,5R)-5-甲基-2-异丙基环己酯
  参考文献：
  名称：

  约束驱动创新指导下的草硫杂环戊烷药物中间体的合成

  摘要：

  开发了一条用于合成拉米夫定（3TC）和恩曲他滨（FTC）的氧杂硫杂环戊烷中间体的新路线。我们通过将自己局限于低成本，可广泛获得的起始材料来开发提出的路线，我们将其称为以供应为中心的合成。使用亚硫酰氯化学从无环前体构建氧杂硫杂环戊烷的骨架。这种键结构的选择使得能够使用氯乙酸，乙酸乙烯酯，硫代硫酸钠和水来生产氧杂硫杂环戊烷。

  DOI：

  10.1021/acs.oprd.0c00145

文献信息

• 一种恩曲他滨的合成方法
  申请人：武汉工程大学

  公开号：CN110467608B

  公开（公告）日：2023-04-07

  本发明提供一种恩曲他滨的合成方法，该合成方法以廉价易得的二卤乙酸为原料，与L‑薄荷醇缩合后，经水解得到乙醛酸薄荷酯，接着与2,5‑二羟基‑1,4‑二噻烷缩合，经卤化后与硅烷化的5‑氟胞嘧啶偶联，还原，与水杨酸成盐得到恩曲他滨水杨酸盐，最后重结晶得到光学纯的恩曲他滨，整个合成过程中所用原料低廉易得，合成工艺简单，合成条件温和，使得本发明的恩曲他滨的合成成本大大降低，且本发明中各原料反应选择性好，利用率高，所得恩曲他滨的收率较高，同时，在合成过程中手性底物容易除去，产生的三废污染物少，适合恩曲他滨工业化大规模生产。
• PROCESS FOR PREPARATION OF CIS-NUCLEOSIDE DERIVATIVE
  申请人：Shankar Rama

  公开号：US20110282046A1

  公开（公告）日：2011-11-17

  The present invention relates to a novel and stereoselective synthetic process for the preparation of optically active cis-nucleoside derivatives of compound of Formula (I), wherein R 3 represents H, F, Cl, C 1-16 alkyl.

  本发明涉及一种新颖的和立体选择性的合成过程，用于制备化合物的光学活性顺式核苷衍生物，其中R3代表H、F、Cl、C1-16烷基。
• [EN] PROCESS AND INTERMEDIATES FOR THE PREPARATION OF SUBSTITUTED 1, 3-OXATHIOLANES, ESPECIALLY LAMIVUDINE<br/>[FR] PROCÉDÉS INTERMÉDIAIRES POUR LA PRÉPARATION DE 1,3-OXATHIOLANES SUBSTITUÉS, NOTAMMENT DE LAMIVUDINE
  申请人：RANBAXY LAB LTD

  公开号：WO2009069012A1

  公开（公告）日：2009-06-04

  The present invention relates to process and intermediates for the preparation of substituted 1,3-oxathiolanes. The present invention specifically relates to a process for the preparation of lamivudine.

  本发明涉及用于制备取代的1,3-噻烷的过程和中间体。本发明具体涉及一种用于制备拉米夫定的过程。
• 具有生物活性的芳氧苯氧烷酸衍生物及其制 备方法
  申请人：三峡大学

  公开号：CN106632293B

  公开（公告）日：2019-02-26

  本发明公开了芳氧苯氧烷酸衍生物及其除草活性，其化学结构式如式I或Ⅱ所示：式中，R1为氢或C1～C3烷基或C1～C3卤代烷基中的任意一种；X为氮或碳；X1、X2、X3为氢或氟或氯或溴或碘或三氟甲基或氰基或硝基中的任意一种。本发明还涉及含有上述化合物的组合物及芳氧苯氧烷酸衍生物在农用除草剂方面的应用，有的化合物具有很高的除草活性，在5克/亩用量下可以获得很好的防治效果。
• 芳氧苯氧烷酸衍生物及其医药用途
  申请人：三峡大学

  公开号：CN108218847B

  公开（公告）日：2021-03-23

  本发明公开了芳氧苯氧烷酸衍生物及其医药活性，其化学结构式如式I所示：式中，R1为氢或C1～C3烷基或C1～C3卤代烷基中的任意一种；X为氮或碳；X1、X2为氢或氟或氯或溴或碘或三氟甲基或氰基或硝基中的任意一种。本发明还涉及含有上述化合物的组合物及芳氧苯氧烷酸衍生物在抗肿瘤方面的应用。