(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate | CAS No. 15717-45-0

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate

Basic Information

CAS Number

15717-45-0

Molecular Formula

C16H18BrN5O8

Molecular Weight

488.25 g/mol

AD

Basic Physical Properties

Melting Point

215-218°C

Boiling Point

673.5°Cat760mmHg

Density

1.94

Flash Point

361.1°C

Refractive Index

1.723

CC(=O)OCC1C(C(C(O1)N2C3=C(C(=O)NC(=N3)N)N=C2Br)OC(=O)C)OC(=O)C

InChI

InChI=1S/C16H18BrN5O8/c1-5(23)27-4-8-10(28-6(2)24)11(29-7(3)25)14(30-8)22-12-9(19-15(22)17)13(26)21-16(18)20-12/h8,10-11,14H,4H2,1-3H3,(H3,18,20,21,26)/t8-,10-,11-,14-/m1/s1

InChIKey

JLZCAXCVNVVXJL-IDTAVKCVSA-N

LogP

-0.21179999999999966

Topological Polar Surface Area

177.72000000000003 Ų

Hydrogen Bond Donor/Acceptor

3 / 13

Complexity

779

Synonyms & References

English

  • (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate
  • Guanosine, 8-bromo-, 2',3',5'-triacetate
  • [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-amino-8-bromo-6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
  • 2',3',5-Tri-O-acetyl-8-bromoguanosine
  • JLZCAXCVNVVXJL-IDTAVKCVSA-N
  • E85512
  • 8-Bromo-2',3',5'-tri-O-acetylguanosine
  • 8-Bromoguanosine 2',3',5'-triacetate
  • NS00052009
  • (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
  • NSC 174056
  • (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyldiacetate
  • 15717-45-0
  • NSC 79210
  • 2',3',5'-Tri-O-acetyl-8-bromoguanosine
  • MFCD00057036
  • EINECS 239-810-6
  • A809817
  • SCHEMBL4378875
  • AKOS027320601
  • 2',3',5'-Tri-O-acetyl-8-bromoadenosine
  • Guanosine, 8-bromo-,2',3',5'-triacetate
  • 2',3',5'-Tri-O-acetyl-8-broMoguanosine
  • 2',3',5-TRI-O-ACETYL-8-BROMOGUANOSINE
  • 8-BROMO-2’,3’,5’-TRI-O-ACETYLGUANOSINE
  • 2',3',5'.-tri-O-acetyl-8-bromoguanosine
  • 2',3',5'-tri-O-acetyl-2-bromoguanosine
  • 2',3',5'-Tri-O-acetyl-8-bromo-D-guanosine
  • 2'-O,3'-O,5'-O-Triacetyl-8-bromoguanosine
  • 8-bromoguanosine 2',3',5'-triacetate

MDL Number

MFCD00057036

FAQ

What are the physical and chemical properties of (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 15717-45-0)?

This compound is a white crystalline solid with a molecular weight of approximately 512.16 g/mol. It is sparingly soluble in water but soluble in organic solvents like ethyl acetate and dichloromethane. The compound is highly reactive and exhibits strong nucleophilic and electrophilic behavior due to its functional groups.

How is (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 15717-45-0) typically synthesized?

This compound is typically synthesized via a multi-step reaction involving the protection of the purine ring with an acetate ester, followed by acetylation of the tetrahydropyran moiety. The reaction is catalyzed by a suitable acid or base, and the overall yield is around 70-80%. The key steps include protecting group installation, acylation, and deprotection.

What industries use (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 15717-45-0)?

This compound is primarily used in the pharmaceutical industry for the development of novel therapeutic agents. Due to its specific chemical structure, it may also find applications in the development of sensors and semiconductors, although its use in these areas is more limited.

What precautions should be taken when handling (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 15717-45-0)?

When handling this compound, appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat should be worn. Operations should be conducted in a well-ventilated fume hood to avoid inhalation of vapors. In case of skin contact, immediately wash with soap and water. For spills, use appropriate spill cleanup kits and follow the Material Safety Data Sheet (MSDS) for disposal instructions.

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