N2-异丁酰基鸟苷一水合物 | 64350-24-9

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷中间体
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N2-异丁酰基鸟苷一水合物
• 中文别名: N2-异丁酰鸟苷
• 英文名称: N²-isobutyryl-2'-deoxyguanosine
• 英文别名: N²-isobutyrylguanosine；N-isobutyrylguanosine；N-Isobutyrylguanosine；N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 64350-24-9
• 化学式: C₁₄H₁₉N₅O₆
• 分子量: 353.335
• InChiKey: OXTYJSXVUGJSGM-HTVVRFAVSA-N

物化性质

• 熔点：
  148 °C
• 密度：
  1.82±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  在常温常压下稳定，应远离氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

安全信息

• 海关编码：
  29389090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

N2-Isobutyrylguanosine Monohydrate Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
N2-Isobutyrylguanosine Monohydrate
Product name:

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
N2-Isobutyrylguanosine Monohydrate
Components:
Percent: ....
CAS Number: 64350-24-9
Chemical Formula: C14H19N5O6·H2O

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
N2-Isobutyrylguanosine Monohydrate

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Almost white
Odour: No data available
pH: No data available
Melting point/freezing point:148°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents] No data available
N2-Isobutyrylguanosine Monohydrate

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
N2-Isobutyrylguanosine Monohydrate

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

N2-异丁酰基鸟苷一水合物是一种重要衍生物，作为食品和医药产品的重要中间体，它可以用于合成食品增鲜剂如5’-鸟苷酸二钠、呈味核苷酸二钠以及核苷类抗病毒药物利巴韦林和阿昔洛韦等。

合成方法

N2-异丁酰基鸟苷一水合物可以通过以下两种方法制备：以鸟苷为原料与异丁酰氯反应，得到目标产物；或者以鸟苷与异丁酸酐作为起始物料，经缩合反应合成目标化合物。具体合成反应式如下图所示。

反应信息

• 作为反应物：
  描述：

  N2-异丁酰基鸟苷一水合物 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷
  参考文献：
  名称：

  3'-叠氮基-2',3'-双脱氧鸟苷衍生物的改进和可靠合成

  摘要：

  描述了 N2-protected-3'-azido-2',3'-dideoxyguanosine 20 和 23 的改进合成。2'-O-烷基（和/或芳基）磺酰基-5'-二甲氧基三苯甲基鸟苷脱氧结合[1,2]-氢化物移位重排得到受保护的9-（2-脱氧-苏式-戊呋喃糖基）鸟嘌呤（10、12和16)。这种重排使用三异丁基硼氢化锂 (l-Selectride®) 以高收率和高立体选择性完成。化合物 10、12 和 16 被转化为 3'-O-甲磺酸盐（18 和 21），可用于 3'-取代。通过用叠氮化锂处理 18 和 21 获得 3'-叠氮基核苷。该过程具有良好的总产率，可重现。†为了纪念和庆祝 Leroy B. Townsend 教授 70 岁生日。

  DOI：

  10.1081/ncn-120027826
• 作为产物：
  描述：

  鸟苷 在 吡啶 、 水 作用下， 反应 24.0h， 生成 N2-异丁酰基鸟苷一水合物
  参考文献：
  名称：

  关键 Ulevostinag 亚基的千克级合成的发展第 I 部分：从鸟苷中获取酮核苷中间体

  摘要：

  描述了 Ulevostinag (MK-1454) 关键片段的千克级合成，Ulevostinag 是干扰素基因 (STING) 刺激物的环状二核苷酸激动剂。Ulevostinag 包含通过两个P连接在一起的两个非天然核苷衍生物-手性硫代磷酸酯基团。用于制备这些核苷之一的策略，即 3'-deoxy-3'-α-fluoro-guanosine (3'-FG)，取决于关键酮-核苷衍生物的非对映选择性 α-氟化，然后是底物-定向还原酮。在此，我们描述了这种中间体（一种来自鸟苷的 3'-脱氧-2'-酮-鸟苷衍生物）稳健且可扩展合成的开发。该方法的显着特征包括将鸟苷的 2' 和 3'-醇基激活为双甲苯磺酸盐，这使得区域选择性 E2 消除能够同时使 3'-位脱氧并产生 2'-酮。

  DOI：

  10.1021/acs.oprd.2c00397

文献信息

• Regioselective protection of carbohydrate derivatives.
  作者：Shigeyoshi Nishino、Hatsuko Takamura、Yoshiharu Ishido

  DOI：10.1016/s0040-4020(01)87616-x

  日期：1986.1

  A simple treatment of fully aroylated purine and pyrimidine ribo-nucleosides with pulverized potassium tert-butoxide in tetrahydrofuran (THF) or dichloromethane under a controlled condition gave a mixture of the corresponding di-O-aroyl derivatives in which 2'-OH derivatives are preponderant over 3'-OH derivatives; 3',5'-di-O-benzoyluridine, N4, 3', 5'-tribenzoylcytidine, N4, 3', 5'-tri-o-toluoylcytidine

  在控制条件下，在四氢呋喃（THF）或二氯甲烷中，用粉碎的叔丁醇钾简单地处理完全芳基化的嘌呤和嘧啶核糖核苷，得到相应的二-O-芳酰基衍生物的混合物，其中2'-OH衍生物占优势超过3'-OH衍生物；3' ，5'-二-O- benzoyluridine，N 4，3' ，5'-tribenzoylcytidine，N 4，3' ，5'-三-邻- toluoylcytidine，N 2，3' ，5'-tribenzoylguanosine，和获得N 2-异丁酰基-3'，5'-二-O-苯甲酰基鸟苷结晶，产率分别为80％，78％，72％，67％和65％。
• Synthesis and antibacterial activity of 5′-tetrachlorophthalimido and 5′-azido 5′-deoxyribonucleosides
  作者：Robert Van Ostrand、Casey Jacobsen、Alicia Delahunty、Carley Stringer、Ryan Noorbehesht、Haidi Ahmed、Ahmed M. Awad

  DOI：10.1080/15257770.2016.1250906

  日期：2017.3.4

  ABSTRACT Reported is an efficient synthesis of adenyl and uridyl 5′-tetrachlorophthalimido-5′-deoxyribonucleosides, and guanylyl 5′-azido-5′-deoxyribonucleosides, which are useful in solid-phase synthesis of phosphoramidate and ribonucleic guanidine oligonucleotides. Replacement of 5′-hydroxyl with tetrachlorophthalimido group was performed via Mitsunobu reaction for adenosine and uridine. An alternative

  摘要 报道了腺苷和尿苷基 5'-四氯邻苯二甲酰亚胺-5'-脱氧核糖核苷和鸟苷酰 5'-叠氮基-5'-脱氧核糖核苷的有效合成，可用于固相合成氨基磷酸酯和核糖核胍寡核苷酸。通过腺苷和尿苷的光信反应，用四氯邻苯二甲酰亚胺基团取代 5'-羟基。另一种方法用于鸟苷，用叠氮基取代 5'-羟基。将所得化合物转化为 5'-氨基-5'-脱氧核糖核苷用于寡核苷酸合成。合成中间体被测试为针对六种细菌菌株的抗微生物剂。所有含有 2',3'-O-异丙基保护基团的类似物均显示出对脑膜炎奈瑟菌的抗菌活性，
• [EN] MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE<br/>[FR] OLIGONUCLÉOTIDES MODIFIÉS ET MÉTHODES D'UTILISATION
  申请人：ALIOS BIOPHARMA INC

  公开号：WO2018053185A1

  公开（公告）日：2018-03-22

  Modified oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of making and use, e.g., against HBV are disclosed.

  修改的寡核苷酸包括在2'和/或3'位置进行修饰的方法以及制备和使用方法，例如用于对抗HBV的方法。
• [EN] BICYCLIC PEPTIDE LIGAND STING CONJUGATES AND USES THEREOF<br/>[FR] CONJUGUÉS LIGANDS PEPTIDIQUES BICYCLIQUES ET LEURS UTILISATIONS
  申请人：BICYCLERD LTD

  公开号：WO2019034866A1

  公开（公告）日：2019-02-21

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用方法。
• Scalable synthesis of substituted 2,7-dimethyl-9-phenylxanthen-9-ol (DMPx-OH): useful for the preparation of crystalline 5′-O-DMPx-protected nucleosides
  作者：Shyamapada Banerjee、P. Srishylam、S. Rajendra Prasad、Michael T. Migawa、Eric E. Swayze、Yogesh S. Sanghvi

  DOI：10.1016/j.tetlet.2012.06.081

  日期：2012.8

  A convenient single-step synthesis of several 2,7-dimethyl-9-phenylxanthen-9-ol (DMPx-OH) analogs has been accomplished using a Friedel–Crafts reaction. Treatment of various DMPx-OH with unprotected 2′-O-methoxyethyl-ribonucleosides (MOE) in the presence of B(C6F5)3, as a Lewis Acid catalyst, furnished 5′-O-protected derivatives of 2′-MOE-ribonucleosides in good yields. The deprotection of the DMPx

  使用Friedel-Crafts反应已经完成了几种2,7-二甲基-9-苯基黄嘌呤9-醇（DMPx-OH）类似物的便捷一步合成。在路易斯酸催化剂的B（C 6 F 5）3存在下，用未保护的2' - O-甲氧基乙基-核糖核苷（MOE）处理各种DMPx-OH ，得到5'- O-保护的2'-衍生物MOE-核糖核苷产率高。DMPx基团的脱保护是通过在非常温和的条件下进行酸水解来实现的。在合成的五个DMPx类似物中，2,7-二甲基-9-（4-硝基苯基）氧杂蒽-9-基团提供了结晶产物，使得能够进行非色谱分离5'- O - Protetcated核苷。