1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione | CAS No. 69256-17-3

1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Basic Information

CAS Number

69256-17-3

Molecular Formula

C10H13FN2O5

Molecular Weight

260.22 g/mol

AD

Basic Physical Properties

CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)F

InChI

InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m1/s1

InChIKey

GBBJCSTXCAQSSJ-JVZYCSMKSA-N

LogP

-1.56628

Topological Polar Surface Area

104.55000000000001 Ų

Hydrogen Bond Donor/Acceptor

3 / 7

Complexity

413

Safety Information

View Safety Information

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral
H315 Causes skin irritation
Skin corrosion/irritation
H319 Causes serious eye irritation
Serious eye damage/eye irritation
H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

  • 2'-Fluorothymidine
  • 37F7D05ANB
  • A855627
  • Z2681892043
  • 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)-5-methyluracil
  • NCGC00253767-01
  • 2'-FLUORO-5-METHYL-1-.BETA.-D-ARABINOFURANOSYLURACIL
  • AS-74549
  • 1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-
  • C76189
  • UNII-37F7D05ANB
  • CAS-163252-36-6
  • 1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  • GBBJCSTXCAQSSJ-JVZYCSMKSA-N
  • 1-(2-FLUORO-2-DEOXY-.BETA.-D-ARABINOFURANOSYL)THYMINE
  • 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)thymine
  • DTXSID2057659
  • 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyluracil
  • J61.760A
  • 1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  • AKOS016844133
  • 2'-Fluoro-5-methylarabinosyluracil
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)-5-methyl-
  • MFCD00870799
  • 2'-Fluoro-5-methyl-1-beta-D-arabinofuranosyluracil
  • 1-(2-Deoxy-2-fluoro-D-arabinofuranosyl)-5-methyluracil
  • NSC 678516
  • 1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
  • CHEMBL475717
  • BDBM50367487

MDL Number

MFCD00870799

FAQ

What are the physical and chemical properties of 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (CAS: 69256-17-3)?

1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione is a white crystalline solid with a molecular weight of approximately 328.12 g/mol. It is poorly soluble in water but slightly soluble in organic solvents like ethanol and acetone. It shows good reactivity towards nucleophilic substitution and exhibits stability under acidic conditions but is sensitive to bases. This compound is also known for its antiviral activity.

How is 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (CAS: 69256-17-3) typically synthesized?

1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione is typically synthesized through a multistep process involving the synthesis of the arabinofuranosyl fragment followed by its coupling with the pyrimidine ring. Specific synthetic methods include the use of protecting groups, coupling reagents like HATU, and mild Lewis acids to promote the coupling reaction. The yield is generally around 50-70%, depending on the optimization of reaction conditions.

What industries use 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (CAS: 69256-17-3)?

1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione is primarily used in the pharmaceutical industry for its antiviral activity, particularly against RNA viruses. It can be found in antiviral formulations and is also used in research and development for the study of viral diseases. Additionally, this compound may have applications in the production of nucleoside analogs for chemotherapy and as a building block in the synthesis of other nucleosides.

What precautions should be taken when handling 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (CAS: 69256-17-3)?

When handling 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione, it is essential to wear appropriate personal protective equipment (PPE) including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated fume hood due to its potential for generating toxic fumes. Spills should be cleaned up immediately using appropriate absorbent materials, and the area should be flushed with water. It is crucial to follow safety data sheet (SDS) guidelines and to avoid contact with skin and eyes. Storage should be in a cool, dry place away from direct sunlight and heat sources.

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