2,3'-anhydrothymidine | 15981-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,3'-anhydrothymidine
• 英文别名: (1R,9R,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one
• CAS: 15981-92-7
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: JCSNHEYOIASGKU-BWZBUEFSSA-N

物化性质

• 熔点：
  246-247oC
• 沸点：
  381.8±52.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: 2,3′-Anhydrothymidine
Product name
CAS-No. : 15981-92-7
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C10H12N2O4
Molecular Weight : 224,21 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
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. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

2',3'-无水硫脒和2'-脱氧-3',2-氢-5-甲基尿苷是嘌呤核苷类似物，具有广泛的抗肿瘤活性，尤其针对惰性淋巴系统恶性肿瘤。这些药物通过抑制DNA合成和诱导细胞凋亡等机制发挥抗癌作用。

反应信息

• 作为反应物：
  描述：

  2,3'-anhydrothymidine 在 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate 、 sodium hydride 作用下， 以 mineral oil 为溶剂， 反应 0.08h， 以93%的产率得到司他夫定
  参考文献：
  名称：

  Synthesis of nucleoside-based antiviral drugs in ionic liquids

  摘要：

  Nucleoside-based antiviral drugs have been synthesized using imidazolium-based ionic liquids as reaction medium. The ionic liquids were proved to be better solvents for all the nucleoside in terms of solubility and reaction medium as compared to conventional molecular solvents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.090
• 作为产物：
  描述：

  beta-胸苷 在 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2,3'-anhydrothymidine
  参考文献：
  名称：

  胸腺嘧啶一步转化为2,3'-脱水衍生物

  摘要：

  大约在2,3'中获得了胸苷的2,3'-脱水衍生物。通过一锅转化（包括串联的Mitsunobu反应）可达到80％的收率。

  DOI：

  10.1039/c39900000801

文献信息

• Radiosynthesis of [18F]-Labelled Pro-Nucleotides (ProTides)
  作者：Alessandra Cavaliere、Katrin C. Probst、Stephen J. Paisey、Christopher Marshall、Abdul K. H. Dheere、Franklin Aigbirhio、Christopher McGuigan、Andrew D. Westwell

  DOI：10.3390/molecules25030704

  日期：——

  obtained via a late stage [18F]fluorination in radiochemical yields (RCY) of 15–30% (n = 5, decay-corrected from end of bombardment (EoB)), with high radiochemical purities (97%) and molar activities of 56 GBq/μmol (total synthesis time of 130 min.). The 2′-[18F]FIAU ProTide was obtained via an early stage [18F]fluorination approach with an RCY of 1–5% (n = 7, decay-corrected from EoB), with high radiochemical

  氨基磷酸酯前核苷酸（ProTides）彻底改变了抗病毒和抗癌核苷疗法领域，克服了核苷疗法的主要局限性，取得了临床和商业上的成功。尽管ProTide技术已转化为临床，但仍存在未解决的体内药代动力学和药效学问题。使用 [18F] 标记模型 ProTides 的正电子发射断层扫描 (PET) 成像可以直接解决关键的机制问题并预测对 ProTide 治疗的反应。在这里，我们报告了首次放射化学合成[18F]ProTides作为PET成像的新型探针。作为概念证明，两种化学性质不同的放射性标记 ProTides 已按照不同的放射合成方法合成为 3'- 和 2'-氟化 ProTides 的模型。3'-[18F]FLT ProTide 通过后期 [18F]氟化获得，放射化学产率 (RCY) 为 15–30%（n = 5，从轰击结束 (EoB) 开始进行衰变校正），具有高放射化学产率纯度 (97%) 和摩尔活性
• Antiviral activity of 2,3′-anhydro and related pyrimidine nucleosides against hepatitis B virus
  作者：Naveen C. Srivastav、Michelle Mak、Babita Agrawal、D. Lorne J. Tyrrell、Rakesh Kumar

  DOI：10.1016/j.bmcl.2010.08.120

  日期：2010.11

  Various 2,3′-anhydro analogs of 5-substituted 1-(2-deoxy-β-d-lyxofuranosyl)uracils (10–15) and a related 1-(3-O-mesyl-2-deoxy-β-d-lyxofuranosyl) pyrimidine nucleoside analog (18) have been synthesized for evaluation as a new class of potential anti-HBV agents. The compounds 10, 12, and 15 demonstrated most potent anti-HBV activities against duck HBV (DHBV) and human HBV with EC50 values in the range

  各种2,3'-脱水的5-取代的类似物的1-（2-脱氧β- d -lyxofuranosyl）尿嘧啶（10 - 15）和相关的1-（3- ö -mesyl -2-脱氧β- d -lyxofuranosyl）嘧啶核苷类似物（18）已被合成作为一种新型的潜在抗HBV药物进行评估。化合物10，12，和15显示出最有效的抗HBV活性抗鸭HBV（DHBV）和人HBV与EC 50个在2.5-10和5-10微克/毫升，分别范围内的值，在非毒性浓度（CC 50  => 200μg/ mL）。核苷18也显示了对DHBV的显着抗HBV活性，EC 50值为2.5μg/ mL，但是在2.2.15细胞中，其对HBV的活性较弱（EC 50  => 10μg/ mL）。
• A novel one-step procedure for the conversion of thymidine into 2,3′-anhydrothymidine
  作者：T. Sudhakar Rao、Colin B. Reese

  DOI：10.1039/c39890000997

  日期：——

  2,3′-Anhydrothymidine (3) is obtained in ca. 65% yield by heating thymidine (2) with an excess of diphenyl sulphite in dimethylacetamide solution; (3) reacts with lithium azide to give 3′-azido-3′-deoxythymidine [AZT, (1)] in good yield.

  大约在2,3'-脱水胸苷（3）中得到。通过将胸苷（2）与过量的亚硫酸二苯酯在二甲基乙酰胺溶液中加热，产率为65％；（3）与叠氮化锂反应以良好的产率得到3'-叠氮基-3'-脱氧胸苷[AZT，（1）]。
• Nucleosidyl‐<i>O</i>‐Methylphosphonates: A Pool of Monomers for Modified Oligonucleotides
  作者：Dominik Rejman、Milena Masojídková、Ivan Rosenberg

  DOI：10.1081/ncn-200033912

  日期：2004.1.1

  2′‐deoxyribonucleosides, 1‐(2‐deoxy‐β‐D‐threo‐pentofuranosyl)thymine, 5′‐O‐ and 2′‐O‐phosphonomethyl derivatives of 1‐(3‐deoxy‐β‐D‐erythro‐pentofuranosyl)thymine, and 1‐(3‐deoxy‐β‐D‐threo‐pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4‐methoxy‐1‐oxido‐2‐pyridylmethyl ester group, serving also as an intramolecular

  四种天然 2'-脱氧核糖核苷、1-（2-脱氧-β-D-苏式-戊呋喃糖基）胸腺嘧啶、5'-O- 和 2' 的一组独特的 5'-O- 和 3'-O-膦酰基甲基衍生物1-(3-脱氧-β-D-赤型-戊呋喃糖基)胸腺嘧啶和1-(3-脱氧-β-D-苏式-戊呋喃糖基)胸腺嘧啶的-O-膦酰基甲基衍生物已被合成为单体库修饰寡核苷酸的合成。膦酸酯部分用 4-甲氧基-1-氧化-2-吡啶基甲酯基团保护，在偶联步骤中也作为分子内催化剂。
• Synthesis, structure, and biological evaluation of C-2 sulfonamido pyrimidine nucleosides
  作者：Irena Krizmanić、Aleksandar Višnjevac、Marija Luić、Ljubica Glavaš-Obrovac、Mladen Žinić、Biserka Žinić

  DOI：10.1016/s0040-4020(03)00589-1

  日期：2003.6

  The C-2 sulfonamido pyrimidine nucleosides were prepared by opening the 2,2′- or 2,3′-bond in anhydronucleosides under nucleophilic attack of sulfonamide anions. Reaction of the sodium salt of p-toluenesulfonamide or 2-(aminosulfonyl)-N,N-dimethylnicotinamide with 2,2′-anhydro-1-(β-d-arabinofuranosyl)cytosine gave the C-2 sulfonamido derivatives in excellent yields. Ring opening of the less reactive

  通过在磺酰胺阴离子的亲核攻击下在脱水核苷中打开2,2'-或2,3'-键来制备C-2磺酰胺基嘧啶核苷。对甲苯磺酰胺或2-（氨基磺酰基）-N，N-二甲基烟酰胺的钠盐与2，2'-脱水-1-（β-d-阿拉伯呋喃糖基）胞嘧啶的反应以优异的产率得到C-2磺酰胺基衍生物。较低反应性的2,2'-脱水尿苷和2,3'-脱水胸苷的开环可以通过对甲苯磺酰胺的DBU / CH 3 CN活化来完成，从而得到适量的C-2磺酰胺基衍生物。乙酸或ZnBr 2 / CH 2 Cl 2对5-甲基-N 2-甲苯磺酰基-1-（2-脱氧-5- O-三苯甲基-β-d-苏-戊呋喃糖基）异胞嘧啶导致保护基和核苷键均裂解，产生5-甲基-N 2-甲苯磺酰基异胞嘧啶作为主要产品。通过1D和2D NMR实验以及4-亚氨基-N 2-甲苯磺酰基氨基-1-（β-d-阿拉伯呋喃糖基）嘧啶的X射线结构分析证实了所制备的C-2磺酰胺基核苷的结构。两种方法均证