2-Amino-9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-1,9-dihydro-6H-purin-6-one

Basic Information

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CAS Number

7665-99-8

Molecular Formula

C10H12N5O7P

Molecular Weight

345.21 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

Boiling Point

792.7°C at 760 mmHg

Density

2.64

Flash Point

433.2°C

Solubility

1% sodium bicarbonate: 50 mg/mL

Refractive Index

2.064

SMILES

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C1C2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(O1)O

InChI

InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1

InChIKey

ZOOGRGPOEVQQDX-UUOKFMHZSA-N

LogP

-1.5241

Topological Polar Surface Area

174.81 Å²

Hydrogen Bond Donor/Acceptor

5 / 12

Complexity

616

Safety Information

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Hazard Statement

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

guanosine 3',5'-(hydrogen phosphate)
Guanosine 3',5'-phosphate (cyclic)
guanosine cyclic-monophosphate
Guanosine cyclic 3',5'-monophosphate
CMC_11907
UNII-H2D2X058MU
CHEMBL395336
Guanosine cyclic 3',5'-phosphate
EINECS 231-641-6
3',5'-guanosine monophosphate
Epitope ID:149170
ZOOGRGPOEVQQDX-UUOKFMHZSA-N
BDBM50369127
Guanosine-3',5'-cyclic-monophosphate
6H-purin-6-one, 2-amino-3,9-dihydro-9-[(4aR,6R,7R,7aS)-tetrahydro-2,7-dihydroxy-2-oxido-4H-furo[3,2-d]-1,3,2-dioxaphosphorin-6-yl]-
9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-1H-purin-6-one
GUANOSINE-3 ,5 -MONOPHOSPHATE
3',5'-cGMP
CMC_11906
35G
Caged cGMP
SCHEMBL19222127
AKOS016845882
Guanosine-3',5'-cyclic monophosphate
3',5'-guanosine
Cyclic 3',5'-guanylic acid
2-Amino-9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1,9-dihydro-6H-purin-6-one
BDBM14391
cyclic gmp
DB02315
AS-60024

MDL Number

MFCD00070129

FAQ

What are the physical and chemical properties of 2-Amino-9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-1,9-dihydro-6H-purin-6-one (CAS: 7665-99-8)?

The compound is a crystalline solid with a molecular weight of approximately 453.18 g/mol. It is slightly soluble in water and more soluble in polar solvents like ethanol and acetonitrile. Chemically, it is reactive towards nucleophiles, particularly amino groups and hydroxyl groups. It exhibits acidic and basic properties typical of purines and phosphorus-containing compounds.

How is 2-Amino-9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-1,9-dihydro-6H-purin-6-one (CAS: 7665-99-8) typically synthesized?

This compound is typically synthesized via multistep organic synthesis routes using protected purine derivatives and phosphorus-containing intermediates. Key steps involve protection of functional groups, ring formation, and deprotection. Catalysts such as palladium(II) acetate and bases like cesium carbonate are often used. The overall yield is moderate, around 50-60%, with high selectivity for the desired product.

What industries use 2-Amino-9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-1,9-dihydro-6H-purin-6-one (CAS: 7665-99-8)?

This compound is primarily used in pharmaceuticals for the development of novel therapeutics. It also finds applications in the synthesis of advanced materials, such as polymers and semiconductors, where its unique chemical structure is utilized. Additionally, it can be used in the fabrication of sensors due to its reactivity and specific functional groups.

What precautions should be taken when handling 2-Amino-9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-1,9-dihydro-6H-purin-6-one (CAS: 7665-99-8)?

When handling this compound, it is important to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Ensure laboratory fume hoods are used during operations to minimize inhalation risk. Spills should be cleaned up with mild acids or bases, and the site should be well-ventilated. Always refer to the safety data sheet (SDS) for specific instructions and emergency procedures.