ADENOSINE 3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER, TRIETHYLAMMONIUM SALT

Base Information

• Chemical Name: ADENOSINE 3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER, TRIETHYLAMMONIUM SALT
• CAS No.: 151837-09-1
• Molecular Formula: C16H27N6O5PS
• Molecular Weight: 446.46
• Mol file: 151837-09-1.mol

Synonyms:cAMPS-Rp,triethylammonium salt;

Chemical Property of ADENOSINE 3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER, TRIETHYLAMMONIUM SALT

Chemical Property:

• PSA: 186.46000
• LogP: 2.04940
• Storage Temp.: -20°C
• Solubility.: H2O: soluble10mg/mL

Purity/Quality:

98%Min ^*data from raw suppliers

cAMPS-Rp, triethylammonium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Rp-Cyclic AMPS acts as a non-hydrolyzable phosphorothioate analog of cAMP, a competitive inhibitor of cAMP-dependant protein kinases used to distinguish between cyclic AMP-dependant and cyclic AMP-independant contractile coupling mechanisms.

Technology Process of ADENOSINE 3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER, TRIETHYLAMMONIUM SALT

There total 9 articles about ADENOSINE 3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER, TRIETHYLAMMONIUM SALT which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2',3'-Bis-O-(methoxyacetyl)-6-N-(9-phenylxanthen-9-yl)adenosine 5'-phosphorodithioate O-(benzotriazol-1-yl) ester triethylammonium salt → (Rp)-adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt (151837-09-1)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. NaOH / dioxane / 16 h / Ambient temperature

2: pyridine / 16 h / Ambient temperature

3: pyridine / 2 h / Ambient temperature

4: Et₄NF, AcOH / acetonitrile / 48 h / Ambient temperature

5: 2.) H₂O / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 10 min

6: 1.) aq. NaOH, 2.) aq. HCl / 1.) dioxane, r.t., 16 h, 2.) r.t., 40 min

With pyridine; hydrogenchloride; sodium hydroxide; water; tetraethylammonium fluoride; acetic acid; In 1,4-dioxane; acetonitrile;

Reference yield:

triacetyladenosine (7387-57-7,953089-09-3) → (Rp)-adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt (151837-09-1)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 2 h / 90 °C

2: NH₃ / methanol / 16 h / Ambient temperature

3: pyridine / 16 h / Ambient temperature

4: pyridine / 2 h / Ambient temperature

5: Et₄NF, AcOH / acetonitrile / 48 h / Ambient temperature

6: 2.) H₂O / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 10 min

7: 1.) aq. NaOH, 2.) aq. HCl / 1.) dioxane, r.t., 16 h, 2.) r.t., 40 min

With pyridine; hydrogenchloride; sodium hydroxide; ammonia; water; tetraethylammonium fluoride; acetic acid; In methanol; acetonitrile;

Reference yield:

6-N-(9-Phenylxanthen-9-yl)adenosine (174019-04-6) → (Rp)-adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt (151837-09-1)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 16 h / Ambient temperature

2: pyridine / 2 h / Ambient temperature

3: Et₄NF, AcOH / acetonitrile / 48 h / Ambient temperature

4: 2.) H₂O / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 10 min

5: 1.) aq. NaOH, 2.) aq. HCl / 1.) dioxane, r.t., 16 h, 2.) r.t., 40 min

With pyridine; hydrogenchloride; sodium hydroxide; water; tetraethylammonium fluoride; acetic acid; In acetonitrile;

upstream raw materials:

triacetyladenosine

2',3'-Bis-O-(methoxyacetyl)-6-N-(9-phenylxanthen-9-yl)adenosine

6-N-(9-Phenylxanthen-9-yl)adenosine

(2R,3S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[6-(9-phenyl-9H-xanthen-9-ylamino)-purin-9-yl]-tetrahydro-furan-3,4-diol

Refernces