5'-对甲苯磺酸腺苷 | 5135-30-8

• 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: 5'-对甲苯磺酸腺苷
• 中文别名: 5'-对甲苯磺酰氯腺苷；5’-对甲苯磺酸腺苷；5"-对甲苯磺酸腺苷
• 英文名称: 5'-tosyladenosine
• 英文别名: 5′-O-(p-toluenesulfonyl)adenosine；5'-O-(toluenesulfonyl)adenosine；5'-O-toluenesulphonyladenosine；5'-Deoxy-5'-tosyladenosine；5'-O-tosyladenosine；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 5135-30-8
• 化学式: C₁₇H₁₉N₅O₆S
• 分子量: 421.434
• InChiKey: CAXLRAROZXYOHH-LSCFUAHRSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  760.1±70.0 °C(Predicted)
• 密度：
  1.3663 (rough estimate)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）
• 稳定性/保质期：

  常温常压下稳定，应避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  10

安全信息

• 安全说明：
  S24/25
• 海关编码：
  29349990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封保存，存放在阴凉干燥的仓库中。冷藏时温度应保持在-20°C。

SDS

Name:	5 -Tosyladenosine 99+% Material Safety Data Sheet
Synonym:	Adenosine 5'-tosylat
CAS:	5135-30-8

Section 1 - Chemical Product MSDS Name:5 -Tosyladenosine 99+% Material Safety Data Sheet
Synonym:Adenosine 5'-tosylat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5135-30-8	5'-Tosyladenosine	99+	225-883-1

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Antidote: None reported.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Deep freeze (below -20C).

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5135-30-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: @ 760.00mm Hg
Freezing/Melting Point: 151.00 - 153.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C17H19N5O6S
Molecular Weight: 421.42

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5135-30-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5'-Tosyladenosine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 5135-30-8: 2
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5135-30-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5135-30-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

医药中间体

反应信息

• 作为反应物：
  描述：

  5'-对甲苯磺酸腺苷 在 四(四正丁基铵)三磷酸氢盐 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以72%的产率得到5’-三磷酸腺苷
  参考文献：
  名称：

  便捷合成腺苷5'-二磷酸酯，腺苷5'-亚甲基二膦酸酯和腺苷5'-三磷酸酯

  摘要：

  通过用适当的无机盐直接置换，以良好的产率将腺苷5'-甲苯磺酸酯转化为腺苷5'-二磷酸酯（ADP），腺苷5'-亚甲基二膦酸酯和腺苷5'-三磷酸酯（ATP）。

  DOI：

  10.1016/s0040-4039(01)90180-7
• 作为产物：
  描述：

  N6-苯甲酰基腺苷 在 吡啶 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5'-对甲苯磺酸腺苷
  参考文献：
  名称：

  大肠杆菌的核苷转运蛋白NupC和NupG：配体结合所必需的特定结构基序。

  摘要：

  测试了一系列46种天然核苷和类似物（主要是基于腺苷的）作为从大肠杆菌中富集的，与H（+）连接的核苷转运蛋白NupC和NupG吸收[U-（14）C]尿苷的抑制剂。这两个在进化上不相关的转运蛋白显示出相似但不同的抑制模式，揭示了对不同核苷及其类似物的不同选择性。核苷与NupG的结合需要在核糖的C-3'和C-5'位置分别存在羟基，而与NupC的结合仅需要C-3'羟基取代基。核糖部分对于结合NupG的重要性更高，与该蛋白质和寡糖之间的进化关系一致：运输者的主要促进者超家族（MFS）的H（+）同向转运蛋白（OHS）亚家族。对于两种蛋白质，C-3'处的天然α-构型和C-1'处的天然β-构型对于配体结合都是必需的。发现腺苷的咪唑环中的N-7和C-6的氨基对于结合并不重要，并且两个转运蛋白都显示出C-6 / N取代的灵活性。N-1和N-3中的一个或两个对腺苷类似物与NupC的结合很重要，但对NupG的结合

  DOI：

  10.1039/b414739a

文献信息

• Nucleic Acid Related Compounds. 105. Synthesis of 2‘,3‘-Didehydro-2‘,3‘-dideoxynucleosides from Ribonucleoside Cyclic 2‘,3‘-(Sulfates or Phosphates) or 2‘,3‘-Dimesylates via Reductive Elimination with Sodium Naphthalenide¹
  作者：Morris J. Robins、Elzbieta Lewandowska、Stanislaw F. Wnuk

  DOI：10.1021/jo981013m

  日期：1998.10.1

  gave the 2',3'-unsaturated nucleosides. Parallel treatment of adenosine cyclic 2',3'-phosphate gave the 2',3'-olefin. The adenine, hypoxanthine, and 2-amino-6-methoxypurine 2',3'-didehydro-2',3'-dideoxynucleosides were prepared efficiently (40-60% overall yields of crystalline, analytically pure products; 3-5 steps, some combined into one-flask procedures) by treatment of 5'-O-protected 2',3'-di-O-mesylribonucleosides

  用亚硫酰氟处理嘌呤核糖核苷导致形成环状2'，3'-亚硫酸酯。5'-羟基的乙酰化和Sharpless氧化（NaIO（4）/ RuCl（3））得到环状2'，3'-硫酸酯衍生物。用亚硫酰氯处理5'-O-甲硅烷基保护的核糖核苷，然后氧化，得到了环状2'，3'-硫酸盐的另一种途径。用萘钠（THF / -50℃）还原消除，得到2′，3′-不饱和核苷。腺苷环2'，3'-磷酸的平行处理得到2'，3'-烯烃。有效地制备了腺嘌呤，次黄嘌呤和2-氨基-6-甲氧基嘌呤2'，3'-二氢-2'，3'-二脱氧核苷（结晶，分析纯产品的总收率为40-60％； 3-5个步骤，通过将5'-O-保护的2'，3'-di-O-甲磺酰基核糖核苷用萘钠处理来将它们合并成一个烧瓶。反应是在环境温度或低于环境温度的条件下使用容易获得的试剂和标准实验室条件进行的。
• Reaction of adenine nucleosides, tosylated in the carbohydrate moiety, with lithium triethylborohydride
  作者：Piet Herdewijn

  DOI：10.1016/s0040-4020(01)89533-8

  日期：1989.1

  The reaction of lithium triethylborohydride with the 2′,3′-di-O-p-tolyl-sulphonyl derivatives of 9-/bg-D-ribofuranosyladenine, 9-β-D-arabinofuranosyl-adenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied. The reaction of 2′,3′-di-O-p-tolysulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D--pentofuranosyl)adenine. This rearrangement reaction was used for the synthesis of 9-(3

  三乙基硼氢化锂与9- / bg-D-D-呋喃核糖基腺嘌呤，9-β-D-阿拉伯呋喃糖基腺嘌呤，9-β-D-木呋喃基腺嘌呤和9的2'，3'-二-Op-甲苯基-磺酰基衍生物的反应研究了-β-D-呋喃呋喃糖基腺嘌呤。2′，3′-二-Op-甲苯磺酰腺苷与LiEt 3 BH的反应得到9-（3-脱氧-β-D-戊呋喃糖基）腺嘌呤。该重排反应用于从2'，3'，5'-三-Op-甲苯磺酰赖氨酸腺苷一步合成9-（3,5-二脱氧-β-D-戊呋喃糖基）腺嘌呤，产率为58％。
• 2-Trimethylsilylethyl Sulfides in the von Braun Cyanogen Bromide Reaction:  Selective Preparation of Thiocyanates and Application to Nucleoside Chemistry
  作者：Stéphane Chambert、François Thomasson、Jean-Luc Décout

  DOI：10.1021/jo016200q

  日期：2002.3.1

  Mixed 2-(trimethylsilyl)ethyl sulfides were synthesized and used in the von Braun cyanogen bromide reaction for preparing selectively thiocyanates in high yield. We show here that this cleavage reaction is highly selective in methanol in comparison with the reaction of the corresponding non-silyl sulfide analogues. This reaction was applied to the synthesis of nucleosidic thiocyanates such as the new

  合成了混合的2-（三甲基甲硅烷基）乙基硫醚，并将其用于von Braun溴化氰反应中，可高产率选择性地制备硫氰酸盐。我们在这里表明，与相应的非甲硅烷基硫醚类似物的反应相比，这种裂解反应在甲醇中具有很高的选择性。该反应用于合成核苷硫氰酸盐，例如新的核苷14和18，以寻找基于机制的核糖核苷二磷酸还原酶和生物活性分子抑制剂。对于带有羟基官能团和芳环的硫化物来说，选择性裂解是可能的。在相同条件下首次观察到溴化氰氰化和溴化剂与萘氧基己基2-三甲基甲硅烷基乙基硫化物7的反应，用溴化氰在二氯甲烷中处理，选择性地得到对溴萘氧基乙氧基硫氰酸酯10，产率为89％。在二氯甲烷中观察到由溴化氰引发的另一种反应与2-（三甲基甲硅烷基乙基）硫代核苷13，从而以良好的收率得到了相应的对称二硫化物21。
• Synthesis and biochemical properties of chemically stable product analogs of the reaction catalyzed by S-adenosyl-L-methionine decarboxylase
  作者：Michael Kolb、Charles Danzin、Jacqueline Barth、Nicole Claverie

  DOI：10.1021/jm00347a014

  日期：1982.5

  Structural analogues of decarboxylated S-adenosyl-L-methionine (dc-SAM), product of the reaction catalyzed by S-adenosyl-L-methionine decarboxylase (SAM-DC), with modifications in the side-chain portion of the molecule have been synthesized, and their ability to inhibit SAM-DC has been investigated. Mainly, compounds with a nitrogen atom in place of the sulfur were investigated. The data from these

  脱羧化S-腺苷-L-蛋氨酸（dc-SAM）的结构类似物，它是由S-腺苷-L-蛋氨酸脱羧酶（SAM-DC）催化的反应产物，在分子的侧链部分有修饰合成，并研究了其抑制SAM-DC的能力。主要研究了用氮原子代替硫的化合物。这些抑制研究的数据导致了对结合到SAM-DC上所需的结构特征的描绘。结论是，末端伯氨基，末端羧基和the官能度对于在SAM-DC上结合不是必需的。还发现dc-SAM的类似物仍能与该酶形成偶氮甲碱，其中用氮代替硫是唯一的修饰。
• Synthesis of thiazole-4-carboxamide-adenine difluoromethylenediphosphonates substituted with fluorine at C-2′ of the adenosine
  作者：Andrzej Zatorski、Pawell Lipla、Nevena Mollova、Karl H. Schram、Barry M. Goldstein、Kyoichi A. Watanabe、Krzysztof W. Pankiewicz

  DOI：10.1016/0008-6215(93)84063-c

  日期：1993.10

  Synthesis of an analogue 3 of thiazole-4-carboxamide adenine-dinucleotide (TAD) in which the beta-oxygen atom of the pyrophosphate bridge is replaced by a difluoromethylene group has been achieved. Likewise, 2'-deoxy-2'-fluoroadenosine containing analogues of TAD (4) and its difluoromethylenediphosphonate congener (5) have been synthesized. Adenosine 5'-difluoromethylenediphosphonate (8) was prepared

  已经合成了噻唑-4-羧酰胺腺嘌呤二核苷酸（TAD）的类似物3，其中焦磷酸桥的β-氧原子被二氟亚甲基取代。同样，已经合成了含有2'-脱氧-2'-氟腺苷的TAD类似物（4）及其二氟亚甲基二膦酸盐同类物（5）。腺苷5'-二氟亚甲基二膦酸酯（8）是由5'-O-甲苯磺酰基腺苷（6）和三（四正丁基铵）二氟亚甲基二膦酸酯（7）通过改进的Poulter方法制备的。通过用原甲酸三乙酯处理将化合物8转化为2'，3'-环状碳酸酯9。用2'，3'处理9 在DCC存在下，在吡啶中的-O-异亚丙基亚氮杂呋喃（10）得到二核苷酸11和异亚丙基保护的二腺苷四膦酸酯12的混合物。将11脱保护后，所需的β-二氟亚甲基TAD（3）通过HPLC分离为次要化合物。产品。获得了Ap4A的类似物二腺苷四膦酸腺苷12作为主要成分。或者，将2'，3'-O-异丙基亚氮杂呋喃酯（10）甲苯磺酸化，并通过与7偶合，将产物13进一步转化为相应的二

表征谱图