(4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide

Basic Information

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CAS Number

60-92-4

Molecular Formula

C10H12N5O6P

Molecular Weight

329.21 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Agricultural Chemicals Pesticides Insecticides

Basic Physical Properties

Physical State

Powder

Melting Point

220°C

Boiling Point

701.5°C at 760 mmHg

Density

2.4700

Water Solubility

50 mg/mL

Flash Point

378 °C

Solubility

H2O: 10 mg/mL pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble., clear, colorless

Specific Rotation

-53.7 º (c=0.7,water)

SMILES

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c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)N

InChI

InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChIKey

IVOMOUWHDPKRLL-KQYNXXCUSA-N

LogP

-0.8174000000000003

Topological Polar Surface Area

154.84 Å²

Hydrogen Bond Donor/Acceptor

4 / 11

Complexity

498

Safety Information

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Hazard Statement

H314 Causes severe skin burns and eye damage
Skin corrosion/irritation

H318 Causes serious eye damage
Serious eye damage/eye irritation

Hazard Class

Class 8 Class 8

Storage Conditions

-20℃

Synonyms & References

English

Adenosine Cyclophosphate
cyclic amp
Adenosine 3',5'-phosphate
5'-Cyclic Monophosphate
Dimethylaminopyridine
Adenosine 3',5'-Cyclic Monophosphate Hydrate
Adenosine 3',5'-cyclic monophosphate
Adenosine 3',5'-cyclic phosphate (6CI)
Adenosine-3',5'-cyclophosphate
Adenosine-3’,5’-cyclic Monophosphate
Adenosine 3',5'-cyclophosphate
Adenosine 3‘,5‘-cyclic monophosphate
cAMP
3',5'-cAMP Hydrate
3',5'-Cyclic AMP Hydrate
3'-5' Cyclic adenosine monophosphate
3',5'-cyclic AMP
cyclic 3',5'-AMP
Adenosine cyclic monophosphate
cyclic 3',5'-Adenylic acid
Adenosine 3',5'-monophosphate
Cyclic Adenosine Monophosphate
cyclic Adenosine 3',5'-phosphate
Cyclic adenylic acid
Adenosine cyclic 3',5'-monophosphate
3',5'-AMP
cyclic Adenosine 3',5'-monophosphate
Adenosine cyclic 3',5'-phosphate
adenosine-3',5'-cyclic-mono
Adenosine 3’,5’-cyclic monophosphate
Adenosine 3',5'-cyclic phosphate,Adenosine 3',5'-monophosphate,cAMP,Cyclic AMP,Adenosine 3',5'-phosp...

MDL Number

MFCD00005845

FAQ

What is (4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide (CAS: 60-92-4)?

This compound is a complex organic molecule with the chemical formula C10H14N5O7P. It features a purine ring functionalized with amino and hydroxyl groups, along with a phosphonate structure. Known for its stability in aqueous solutions, it is primarily used in pharmaceutical research as a nucleotide analog. Its unique stereochemistry (4aR,6R,7R,7aS) contributes to its biological activity and specificity.

What are the main uses of (4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide (CAS: 60-92-4)?

This compound is primarily utilized in pharmaceutical research for developing antiviral and antitumor agents due to its nucleotide-like structure. It serves as a key intermediate in organic synthesis and is studied for its potential in enzyme inhibition. Additionally, it finds application in biochemical studies to understand purine metabolism and drug-target interactions.

Is (4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide (CAS: 60-92-4) safe?

Safety data for this compound is limited, but it is generally considered to have moderate toxicity. Handling requires protective measures such as gloves, goggles, and a fume hood to avoid skin or respiratory exposure. It is not classified as carcinogenic or mutagenic under standard protocols, but proper ventilation and adherence to OSHA guidelines are recommended for safe use in laboratory settings.

How should (4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide (CAS: 60-92-4) be stored?

Store this compound in a sealed, moisture-proof container at 2-8°C to maintain stability. Protect from light by using amber-colored containers and avoid exposure to air. Due to its hygroscopic nature, it should be kept in a dry environment with desiccants. Long-term storage may require nitrogen atmosphere to prevent degradation.