(S)-1-(6-氨基-9h-嘌呤-9-基)丙烷-2-醇 | 14047-27-9

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: (S)-1-(6-氨基-9h-嘌呤-9-基)丙烷-2-醇
• 中文别名: (S)-9-(2-羟丙基)腺嘌呤；L-(+)-9-(2-羟基丙基)腺嘌呤
• 英文名称: (S)-1-(6-amino-9H-purin-9-yl) propan-2-ol
• 英文别名: (S)-9-(2-hydroxypropyl)adenine；1-(6-amino-purin-9-yl)-propan-2-ol；D-(-)-9-(2-Hydroxypropyl)adenine；L-(+)-9-(2-Hydroxypropyl)adenine；(S)-1-(6-Amino-9H-purin-9-yl)propan-2-ol；(2S)-1-(6-aminopurin-9-yl)propan-2-ol
• CAS: 14047-27-9
• 化学式: C₈H₁₁N₅O
• 分子量: 193.208
• InChiKey: MJZYTEBKXLVLMY-YFKPBYRVSA-N

物化性质

• 熔点：
  183-186°C
• 沸点：
  457.7±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-9-(2-Hydroxypropyl)adenine
Synonyms: (S)-1-(6-Amino-9H-purin-9-yl)propan-2-ol

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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)-9-(2-Hydroxypropyl)adenine
CAS number: 14047-27-9

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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: C8H11N5O
Molecular weight: 193.2

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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：

  (S)-1-(6-氨基-9h-嘌呤-9-基)丙烷-2-醇 在 三甲基氯硅烷 、 三甲基溴硅烷 、 sodium methylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 (S)-9-(2-膦酰甲氧基丙基)腺嘌呤
  参考文献：
  名称：

  Synthesis of Enantiomeric N-(2-Phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine Bases. I. The Stepwise Approach

  摘要：

  (R)和(S)-N-(2-磷酸甲氧基丙基)嘌呤和嘧啶碱（PMP衍生物）对逆转录病毒表现出非常高的活性。本文描述了对映异构体9-(2-磷酸甲氧基丙基)腺嘌呤（I和XXVII）、9-(2-磷酸甲氧基丙基)-2,6-二氨基嘌呤（II和XXXI）、9-(2-磷酸甲氧基丙基)鸟嘌呤（III和XXIX）和1-(R)-(2-磷酸甲氧基丙基)胞嘧啶（XIX）的合成，方法是用双(2-丙基) p-甲苯磺酰氧甲基膦酸酯（X）烷基化对应碱的N保护N-(2-羟基丙基)衍生物，然后逐步去保护中间体的N和O。关键中间体，N-(2-羟基丙基)衍生物IX和XXV，是通过将适当的杂环碱与(R)-或(S)-2-(2-四氢吡喃氧基)丙基 p-甲苯磺酸酯（VII或XXIII）烷基化，并酸水解得到的N-[2-(2-四氢吡喃氧基)丙基]衍生物VIII和XXII。手性合成物是通过对(R)-或(S)-2-(2-四氢吡喃氧基)丙醇（VI或XXI）进行对烯基化制备的，这些化合物可通过还原对映异构烷基2-O-四氢吡喃基乳酸酯V和XXI与双(2-甲氧基乙氧基)铝氢化钠反应得到。这种方法用于合成胞嘧啶、腺嘌呤和2,6-二氨基嘌呤衍生物，而从鸟嘌呤衍生物制备的化合物则是通过2-氨基-6-氯嘌呤中间体的水解制备的。胞嘧啶衍生物IXe也是通过对4-甲氧基-2-嘧啶酮的烷基化后接着中间体IXf的氨解合成的。

  DOI：

  10.1135/cccc19951196
• 作为产物：
  描述：

  1-(6-氨基-9H-嘌呤-9-基)-2-丙酮 在 [RuCl2(benzene)]2 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 sodium formate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以60%的产率得到(S)-1-(6-氨基-9h-嘌呤-9-基)丙烷-2-醇
  参考文献：
  名称：

  The Synthesis of Tenofovir and Its Analogues via Asymmetric Transfer Hydrogenation

  摘要：

  A series of tenofovir analogues with potential antiviral and immunobiologically active compounds were synthesized through an asymmetric transfer hydrogenation reaction from achiral purine derivatives. Up to 97% ee and good to excellent yields were achieved under mild conditions through short reaction steps. The present report suggests an efficient process to acquire tenofovir and its analogues.

  DOI：

  10.1021/ol500583d

文献信息

• 一种合成替诺福韦中间体的方法
  申请人：深圳市万物生医药研发有限公司

  公开号：CN106632340B

  公开（公告）日：2018-09-04

  本发明公开了一种合成替诺福韦中间体的方法，该方法包括：以式2所示的化合物9‑丙烯基腺嘌呤为原料，在(S)‑(‑)‑2,2'‑双(二苯膦基)‑1,1'‑联萘诱导下，与四甲基哌啶氮氧化物发生氧化反应得到式1所示的替诺福韦中间体(R)‑9‑(2‑羟基丙基)腺嘌呤；通过本发明提供的方法制备替诺福韦中间体(R)‑9‑(2‑羟基丙基)腺嘌呤，反应条件更加温和，利于工业化应用推广；目标产物收率高、选择性好；无需使用大量手性化合物，使用少量手性助剂诱导氧化即可，成本更低。
• [EN] ANTIRETROVIRAL ENANTIOMERIC NUCLEOTIDE ANALOGS<br/>[FR] ANALOGUES DE NUCLEOTIDES ENANTIOMERES ANTIRETROVIRAUX
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE ACADEMY OF SCIENCES OF THE CZECH REPUBLIC

  公开号：WO1994003467A2

  公开（公告）日：1994-02-17

  (EN) Resolved enantiomers of formulae (IA) and (IB) wherein B is a purine or pyrimidine base or aza and/or deaza analogs thereof are useful in antiviral pharmaceutical compositions to treat retroviral infections.(FR) Des énantiomères dédoublés des formules (IA) et (IB) où B est une base purique ou pyrimidique, ou bien des analogues aza et/ou désaza de ceux-ci sont utiles dans des compositions pharmaceutiques antivirales pour traiter des infections rétrovirales.

  (中文) 公式（IA）和（IB）的旋光异构体，其中B是嘌呤或嘧啶碱基或其氮杂环和/或去氮杂环衍生物，可用于抗病毒药物组合物中，用于治疗逆转录病毒感染。
• Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: Synthesis, antiviral activity and decomposition study
  作者：Loïc Roux、Stéphane Priet、Nadine Payrot、Clément Weck、Maëlenn Fournier、Fabien Zoulim、Jan Balzarini、Bruno Canard、Karine Alvarez

  DOI：10.1016/j.ejmech.2013.02.039

  日期：2013.5

  9-[2-(Thiophosphonomethoxy)ethyl]adenine [S-PMEA, 8] and (R)-9-[2-(Thiophosphonomethoxy)propyl] adenine [S-PMPA, 9] are acyclic nucleoside thiophosphonates we described recently that display the same antiviral spectrum (DNA viruses) as approved and potent phosphonates PMEA and (R)-PMPA. Here, we describe the synthesis, antiviral activities in infected cell cultures and decomposition study of bis(pivaloyloxymethoxy)-S-PMEA [Bis-POM-S-PMEA, 13] and bis(isopropyloxymethylcarbonyl)-S-PMPA [Bis-POC-S-PMPA, 14] as orally bioavailable prodrugs of the S-PMEA 8 and S-PMPA 9, in comparison to the equivalent "non-thio" derivatives [Bis-POM-PMEA, 11] and [Bis-POC-PMPA, 12]. Compounds 11, 12, 13 and 14 were evaluated for their in vitro antiviral activity against HIV-1-, HIV-2-, HBV- and a broad panel of DNA viruses, and found to exhibit moderate to potent antiviral activity. In order to determine the decomposition pathway of the prodrugs 11, 12,13 and 14 into parent compounds PMEA, PMPA, 8 and 9, kinetic data and decomposition pathways in several media are presented. As expected, bis-POM-S-PMEA 13 and bis-POC-S-PMPA 14 behaved as prodrugs of S-PMEA Sand S-PMPA 9. However, thiophosphonates 8 and 9 were released very smoothly in cell extracts, in contrast to the release of PMEA and PMPA from "non-thio" prodrugs 11 and 12. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Prodrugs of phosphonate nucleotide analogues and methods for selecting and making same
  申请人：GILEAD SCIENCES, INC.

  公开号：EP2682397B1

  公开（公告）日：2017-04-19
• ANTIRETROVIRAL ENANTIOMERIC NUCLEOTIDE ANALOGS
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE ACADEMY OF SCIENCES OF THE CZECH REPUBLIC

  公开号：EP0654037A1

  公开（公告）日：1995-05-24