5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine

Base Information

• Chemical Name: 5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine
• CAS No.: 1802226-78-3
• Molecular Formula: C₁₈H₂₃N₅O₉P₂
• Molecular Weight: 515.356

Synonyms:

Chemical Property of 5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine

Chemical Property:

• Boiling Point: 894.2±75.0 °C(Predicted)
• Density: 1.89±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

PSB12379 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: PSB-12379 is an inhibitor of ecto-5’-nucleotidase (CD73; Kis = 2.21 and 9.03 nM for the recombinant human and rat enzyme, respectively). It is selective for CD73 over human nucleoside triphosphate diphosphohydrolase 1 (NTPDase 1), -2, and -3, ectonucleotide pyrophosphatase/phosphodiesterase family member 1 (ENPP1), -2, and -3 (Kis = >10,000 nM for all), as well as the purinergic P2Y1 and P2Y12 receptors at 10 μM. PSB-12379 inhibits CD73 in isolated human serum with a Ki value of 18.8 nM.

Technology Process of 5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine

There total 6 articles about 5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine 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',5'-tri-O-acetylinosine (3181-38-2) → 5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine (1802226-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; trichlorophosphate / 0.12 h / 20 °C / Inert atmosphere

1.2: 0.22 h / Reflux

2.1: ammonia / methanol / 19 h / 0 - 20 °C

3.1: triethylamine / ethanol / 18 h / 60 °C

4.1: trimethyl phosphite / 0.5 h / Cooling

4.2: 1.25 h / 20 °C / pH 7.4 - 7.6 / Cooling

With trimethyl phosphite; dmap; ammonia; triethylamine; trichlorophosphate; In methanol; ethanol;

DOI:10.1021/acs.jmedchem.5b00802

Reference yield:

6-Chloropurine riboside (2004-06-0) → 5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine (1802226-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / ethanol / 18 h / 60 °C

2.1: trimethyl phosphite / 0.5 h / Cooling

2.2: 1.25 h / 20 °C / pH 7.4 - 7.6 / Cooling

With trimethyl phosphite; triethylamine; In ethanol;

DOI:10.1021/acs.jmedchem.5b00802

Reference yield:

benzylamine (100-46-9) → 5’-[hydrogen P-(phosphonomethyl)phosphonate]N-(phenylmethyl)adenosine (1802226-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / ethanol / 18 h / 60 °C

2.1: trimethyl phosphite / 0.5 h / Cooling

2.2: 1.25 h / 20 °C / pH 7.4 - 7.6 / Cooling

With trimethyl phosphite; triethylamine; In ethanol;

DOI:10.1021/acs.jmedchem.5b00802

upstream raw materials:

P,P'-methanediyl-bis-phosphonic acid tetrachloride

N₆-Benzyladenosine

2',3',5'-tri-O-acetylinosine

2',3',5'-O-triacetyl-6-chloroinosine

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