2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one | CAS No. 26578-09-6

2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one

Basic Information

CAS Number

26578-09-6

Molecular Formula

C10H13N5O5

Molecular Weight

283.24 g/mol

AD

Basic Physical Properties

Density

2.258 g/cm3

C1=NC2=C(N1C3C(C(C(O3)CO)O)O)N=C(NC2=O)N

InChI

InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m0/s1

InChIKey

NYHBQMYGNKIUIF-GIMIYPNGSA-N

LogP

-2.6866999999999988

Topological Polar Surface Area

159.51 Ų

Hydrogen Bond Donor/Acceptor

6 / 10

Complexity

446

Synonyms & References

English

  • E78056
  • AKOS037649163
  • 2-AMINO-9-[(2S,3S,4R,5S)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-1H-PURIN-6-ONE
  • NYHBQMYGNKIUIF-GIMIYPNGSA-N
  • L-GUANOSINE
  • MFCD00064103
  • J-700329
  • 26578-09-6
  • 9-beta-L-Ribofuranosylguanine
  • SCHEMBL329614
  • NSC-816047
  • SCHEMBL17993312
  • BS-16795
  • 2-Amino-9-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3H-purin-6(9H)-one
  • AC-32190
  • 2-amino-9-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
  • NSC816047
  • 2-amino-9-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
  • L-Guanosine
  • 2-amino-9-pentofuranosyl-1,9-dihydro-purin-6-one
  • β-L-GUANOSINE
  • Guanine,9-b-L-ribofuranosyl- (8CI)
  • guanosine
  • guanine riboside
  • vernine
  • Guanozin
  • Guanosin
  • Inosine, 2-amino-
  • Vernine (VAN)
  • 9-beta-D-Ribofuranosylguanine
  • Guanine-9-beta-D-ribofuranoside

MDL Number

MFCD00064103

FAQ

What are the physical and chemical properties of 2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one (CAS: 26578-09-6)?

2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one is a crystalline solid with a molecular weight of approximately 324.32 g/mol. It has a high solubility in water and is slightly soluble in ethanol. The compound is known for its reactivity with nucleophiles and its stability under basic conditions. It is typically used as a building block in synthetic organic chemistry.

How is 2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one (CAS: 26578-09-6) typically synthesized?

2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one is typically synthesized through a multistep process involving the ribosylation of 6-aminopurine using a beta-L-ribonucleoside. Common catalysts include organometallic reagents, and the reaction is often carried out under acidic conditions. The yield can be improved by optimizing the reaction conditions and using high-purity starting materials.

What industries use 2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one (CAS: 26578-09-6)?

2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one is used in the pharmaceutical industry as a precursor for the synthesis of nucleoside analogs, which are important for antiviral and anticancer treatments. It is also employed in the development of biosensors and in the production of nucleoside-based polymers for various applications.

What precautions should be taken when handling 2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one (CAS: 26578-09-6)?

When handling 2-Amino-9-(beta-L-ribofuranosyl)-1,9-dihydro-6H-purin-6-one, it is essential to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. The compound should be stored in a well-ventilated area, preferably in a fume hood, and away from oxidizing agents. In case of a spill, the area should be flushed with water, and the material should be carefully cleaned up according to the safety data sheet (SDS).

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