(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate | CAS No. 16321-99-6

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Basic Information

CAS Number

16321-99-6

Molecular Formula

C16H18ClN5O7

Molecular Weight

427.8 g/mol

AD

Basic Physical Properties

Melting Point

146.0 to 150.0 deg-C

Boiling Point

637°C at 760 mmHg

Flash Point

339°C

Refractive Index

1.69

CC(=O)OCC1C(C(C(O1)N2C=NC3=C2N=C(N=C3Cl)N)OC(=O)C)OC(=O)C

InChI

InChI=1S/C16H18ClN5O7/c1-6(23)26-4-9-11(27-7(2)24)12(28-8(3)25)15(29-9)22-5-19-10-13(17)20-16(18)21-14(10)22/h5,9,11-12,15H,4H2,1-3H3,(H2,18,20,21)/t9-,11-,12-,15-/m1/s1

InChIKey

HLVGVJFVAKPFOZ-SDBHATRESA-N

LogP

0.3857999999999998

Topological Polar Surface Area

157.75000000000006 Ų

Hydrogen Bond Donor/Acceptor

2 / 12

Complexity

655

Synonyms & References

English

  • MFCD03425473
  • 9-(2',3',5'-Tri-O-acetyl-beta-D-ribofuranosyl)-2-amino-6-chloro-(9H)-purine
  • 9-(2',3',5'-Tri-O-acetyl-beta-D-ribofuranosyl)-2-amino-6-chloro-9H-purine
  • (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(2-amino-6-chloropurin-9-yl)oxolan-3-yl acetate
  • C16H18ClN5O7
  • 9H-Purin-2-amine, 6-chloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-
  • AS-7059
  • 2-amino-6-chloro-9-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)purine
  • SCHEMBL1120550
  • 2-Amino-6-chloro-9-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)purine
  • 2',3',5'-Tri-O-acetyl-2-amino-6-chloropurine Riboside
  • 2-Amino-6-chloropurine-9-(2 inverted exclamation mark ,3 inverted exclamation mark ,5 inverted exclamation mark -tri-O-acetyl)-riboside
  • [(2r,3r,4r,5r)-3,4-diacetyloxy-5-(2-amino-6-chloropurin-9-yl)oxolan-2-yl]methyl acetate
  • 2-amino-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-9H-purine
  • ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(2-AMINO-6-CHLORO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER
  • 2',3',5'-Tri-O-acetyl-6-chloro-6-deoxyguanosine
  • 2-amino-6-chloro-9-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl) purine
  • A810454
  • HLVGVJFVAKPFOZ-SDBHATRESA-N
  • 2-Amino-6-chloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine
  • 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-2-amino-6-chloro-9H-purine
  • T2690
  • 2-Amino-6-chloro-9-(2,3,5-tri-O-acetyl-?-D-ribofuranosyl)purine
  • 9-(2,3,5-tri- O-acetyl-beta-D-ribofuranosyl)-2-amino-6-chloro-9H-purine
  • [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-amino-6-chloro-9H-purin-9-yl)oxolan-2-yl]methyl acetate
  • 9H-Purin-2-amine,6-chloro-9-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)-
  • F12905
  • (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyldiacetate
  • (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
  • 2-Chloro-6-amino-9-(2',3',5'-tri-O-acetyl- beta -D-ribofuranosyl)purine
  • AKOS015967409

MDL Number

MFCD03425473

FAQ

What are the physical and chemical properties of (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 16321-99-6)?

This compound is an optically active diacetate derivative of 2-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran. It crystallizes in the form of white needles or fine crystals. The molecular weight is approximately 467.31 g/mol. It is poorly soluble in water but soluble in organic solvents like methanol and acetonitrile. The compound exhibits reactivity typical of acyl groups and amine functionalities, making it suitable for various synthetic transformations.

How is (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 16321-99-6) typically synthesized?

This compound can be synthesized via the condensation of 2-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran with acetic anhydride. Commonly, this is catalyzed by a tertiary amine base such as triethylamine. The reaction typically proceeds with high yield and good selectivity, providing a diacetate product.

What industries use (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 16321-99-6)?

This compound is primarily used in the pharmaceutical industry for its potential as a bioactive molecule with possible therapeutic applications. It may also find utility in the synthesis of other complex organic compounds, particularly those involving purine derivatives, which are important in drug development and molecular biology research.

What precautions should be taken when handling (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (CAS: 16321-99-6)?

When handling this compound, it is important to wear appropriate personal protective equipment (PPE) such as gloves and goggles. Store the compound in a well-ventilated area and use a fume hood during handling or synthesis. In the event of a spill, immediately clean up using appropriate absorbent materials and follow proper disposal protocols as outlined in the Safety Data Sheet (SDS).

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