5-乙酰基-2,3-异亚丙基腺苷酸 | 15888-38-7

• 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: 5-乙酰基-2,3-异亚丙基腺苷酸
• 中文别名: 5'-乙酰基-2',3'-异亚丙基腺苷；5'-O-乙酰基-2'3'-O-异亚丙基腺苷
• 英文名称: 5'-acetyl-2',3'-isopropylideneadenosine
• 英文别名: acetic acid 6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester；5’-O-acetyl-2’,3’-O-isopropylideneadenosine；5'-O-acetyl-2',3'-O,O-isopropylideneadenosine；2',3'-O-isopropylidene-5'-O-acetyladenosine；5'-O-acetyl-2',3'-O-isopropylideneadenosine；5'-acetyl-2',3'-O-isopropylidene adenosine；[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate
• CAS: 15888-38-7
• 化学式: C₁₅H₁₉N₅O₅
• 分子量: 349.346
• InChiKey: AGPPMENETHBDES-IDTAVKCVSA-N

物化性质

• 熔点：
  170-172°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P262
• 危险性描述：
  H302
• 储存条件：
  -20°C

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE,
98%

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
2',3'-O-ISOPROPYLIDENEADENOSINE 15888-38-7 240-026-1 None
5'-MONOACETATE
Formula C15H19N5O5
Molecular Weight 349,3500 AMU

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If not breathing give
artificial respiration. If breathing is difficult, give oxygen.
AFTER SKIN CONTACT
In case of contact, immediately wash skin with soap and copious
amounts of water.
AFTER EYE CONTACT
In case of contact, immediately flush eyes with copious amounts
of water for at least 15 minutes.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
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appropriate foam.
SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear respirator, chemical safety goggles, rubber boots, and
heavy rubber gloves.
METHODS FOR CLEANING UP
Sweep up, place in a bag and hold for waste disposal. Avoid
raising dust. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Avoid inhalation. Avoid contact
with eyes, skin, and clothing. Avoid prolonged or repeated
exposure.
STORAGE
Conditions of Storage: Keep tightly closed. Store in a cool dry
place.

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Safety shower and eye bath. Mechanical exhaust required.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling. Wash contaminated clothing before
reuse.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Respiratory protection is not required. Where
protection is desired, use multi-purpose combination (US) or type
ABEK (EN 14387) respirator cartridges.
Hand Protection: Compatible chemical-resistant gloves.
Eye Protection: Chemical safety goggles.

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9 - Physical and Chemical Properties

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pH N/A
BP/BP Range N/A
MP/MP Range 170,000. - 172,000 °
C.
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
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Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Materials to Avoid: Strong oxidizing agents.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide,
Nitrogen oxides.

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11 - Toxicological Information

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SIGNS AND SYMPTOMS OF EXPOSURE
To the best of our knowledge, the chemical, physical, and
toxicological properties have not been thoroughly investigated.
ROUTE OF EXPOSURE
Skin Contact: May cause skin irritation.
Eye Contact: May cause eye irritation.
Multiple Routes: May be harmful by inhalation, ingestion, or
skin absorption.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and
scrubber. Observe all federal, state, and local environmental
regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-乙酰基-2,3-异亚丙基腺苷酸 在 甲醇 、 水 、 三乙胺 作用下， 以95%的产率得到2',3'-异丙叉腺苷
  参考文献：
  名称：

  Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium

  摘要：

  A straightforward methodology for deacetylation of protected ribonucleosides was developed based on triethylamine-catalyzed solvolysis in aqueous methanol. Reactions are completed in a few minutes under microwave irradiation and the free nucleosides are obtained in high yield after simple evaporation of volatiles. Other important features include the involvement of readily available reagents and the compatibility with diverse functional groups, which make this process very attractive for broad application.

  DOI：

  10.1590/s0103-50532010000500013
• 作为产物：
  描述：

  在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到5-乙酰基-2,3-异亚丙基腺苷酸
  参考文献：
  名称：

  Schwartz试剂促进受保护核苷和核苷酸的化学选择性N-脱乙酰化。

  摘要：

  涉及N-乙酰基的保护和脱保护策略被广泛用于核苷和核苷酸化学中。在本文中，我们提出了一种温和的选择性N-脱乙酰化方法，该方法可通过Schwartz试剂与嘌呤和嘧啶核苷一起使用，与核苷化学中使用的大多数常见保护基团兼容。

  DOI：

  10.1080/15257770.2015.1075552

文献信息

• Solventless Protocol for Efficient Bis-<i>N</i>-Boc Protection of Adenosine, Cytidine, and Guanosine Derivatives
  作者：Siddharth A. Sikchi、Philip G. Hultin

  DOI：10.1021/jo060430t

  日期：2006.8.1

  A solvent-free reaction employing a simple low-energy ball mill apparatus converts the amino groups of adenosine, 2-deoxyadenosine, cytidine, 2-deoxycytidine, guanosine, and 2-deoxyguanosine as well as some of their ribosyl O-protected derivatives to the corresponding bis-N-Boc carbamates. In the case of guanosine compounds, the carbonyl group of the base moiety was also blocked as its O-Boc enol carbonate

  使用简单的低能球磨仪进行的无溶剂反应将腺苷，2-脱氧腺苷，胞嘧啶核苷，2-脱氧胞苷，鸟苷和2-脱氧鸟苷的氨基以及它们的一些核糖基O保护的衍生物转化为相应的bis- N -Boc氨基甲酸酯。在鸟苷化合物的情况下，该碱基部分的羰基也被封闭为其O- Boc烯醇碳酸酯。使用瞬态原位O硅烷化的这种方法的一种变体允许制备bis- N-Boc核苷，其中糖羟基不受保护。除鸟苷化合物外，球磨反应迅速，方便且产率很高。这种高效的方法使用适合进一步合成操作的碱稳定且酸不稳定的基团保护这些核苷的氨基。
• Automated Nanomole-Scale Reaction Screening toward Benzoate Bioisosteres: A Photocatalyzed Approach to Highly Elaborated Bicyclo[1.1.1]Pentanes
  作者：James J. Mousseau、Matthew A. Perry、Mark W. Bundesmann、Gary M. Chinigo、Chulho Choi、Gary Gallego、Robert W. Hicklin、Susan Hoy、David C. Limburg、Neal W. Sach、Yuan Zhang

  DOI：10.1021/acscatal.1c05076

  日期：2022.1.7

  Through the application of high-throughput nanoscale optimization, a mild, photocatalyzed, Minisci-like protocol was developed to access highly functionalized 1,3-disubstituted bicyclopentanes. The benzoate-isosteric compounds were prepared using a readily available organic photocatalyst, mitigating the need for precious metals. The strategy described furnished products in synthetically useful yields

  通过应用高通量纳米级优化，开发了一种温和的、光催化的、类似 Minisci 的协议来获得高度功能化的 1,3-二取代双环戊烷。苯甲酸酯等排化合物是使用容易获得的有机光催化剂制备的，从而减少了对贵金属的需求。该策略以综合有用的产量描述了提供的产品，并被证明可以以并行的药物化学格式执行。
• Protection of the Amino Group of Adenosine and Guanosine Derivatives by Elaboration into a 2,5-Dimethylpyrrole Moiety
  作者：Ireneusz Nowak、Morris J. Robins

  DOI：10.1021/ol035264f

  日期：2003.9.1

  [reaction: see text] Protection of the amino group of adenine and guanine nucleosides was effected by heating the substrates in 2,5-hexanedione. The resulting 2,5-dimethylpyrrole adducts were stable toward bases but were hydrolyzed with TFA/H(2)O to regenerate the amino function.

  [反应：见正文]通过在2，5-己二酮中加热底物来实现对腺嘌呤和鸟嘌呤核苷氨基的保护。所得的2，5-二甲基吡咯加合物对碱稳定，但可与TFA / H（2）O水解以再生氨基功能。
• Clay‐Mediated Selective Hydrolysis of 5′‐<i>O</i>‐Acetyl‐2′,3′‐isopropylidene/Cyclohexylidene Nucleosides
  作者：Mukund K. Gurjar、Dhananjoy Mondal、S. V. Ravindranadh、Mukund S. Chorghade

  DOI：10.1080/00397910600639968

  日期：2006.8

  Abstract A generalized procedure for the selective hydrolysis of 5′‐O‐acetyl‐2′,3′‐isopropylidene/cyclohexylidene nucleosides with a solid catalyst, Montmorillonite K‐10 in refluxing methanol, to furnish 5′‐O‐acetyl‐nucleosides is described.

  摘要 用固体催化剂蒙脱石 K-10 在回流甲醇中选择性水解 5'-O-乙酰基-2',3'-异亚丙基/亚环己基核苷以提供 5'-O-乙酰基核苷的通用程序是描述。
• ANTI-WRINKLE COSMETIC COMPOSITION
  申请人：Dalko Maria

  公开号：US20070237734A1

  公开（公告）日：2007-10-11

  The present invention relates to adenosine derivatives and methods of treating skin using such derivatives.

  本发明涉及腺苷衍生物及使用这些衍生物治疗皮肤的方法。

表征谱图