Phosphomethylphosphonic acid adenosyl ester

Base Information

• Chemical Name: Phosphomethylphosphonic acid adenosyl ester
• CAS No.: 3768-14-7
• Molecular Formula: C11H17 N5 O9 P2
• Molecular Weight: 425.232
• European Community (EC) Number: 223-194-0
• UNII: 0T2A5439OE
• Nikkaji Number: J217.662I
• Wikidata: Q27074395
• RXCUI: 2552302
• Pharos Ligand ID: 3NKT4YC4WTX3
• Metabolomics Workbench ID: 52260
• ChEMBL ID: CHEMBL583969
• Mol file: 3768-14-7.mol

Synonyms:adenosine 5'-methylenediphosphate;adenosine-5 alpha, beta-methylene diphosphonate;adenosine-alpha,beta-methylene diphosphate;alpha,beta-methylene adenosine 5'-diphosphate;alpha,beta-methylene ADP;alpha,beta-methylene-adenosinediphosphate;alpha,beta-methyleneadenosine 5'-diphosphate;alpha,beta-methyleneadenosine-5'-diphosphate;AOPCP;APCP cpd

Chemical Property of Phosphomethylphosphonic acid adenosyl ester

Chemical Property:

• Boiling Point: 895.6°Cat760mmHg
• PKA: 1.62±0.10(Predicted)
• Flash Point: 495.4°C
• PSA: 242.99000
• Density: 2.35g/cm³
• LogP: -1.05390
• Storage Temp.: −20°C
• XLogP3: -4.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 425.05015113
• Heavy Atom Count: 27
• Complexity: 637

Purity/Quality:

98%,99%, ^*data from raw suppliers

MethADP ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(CP(=O)(O)O)O)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)N
• Uses: Adenosine 5′-(α,β-methylene)diphosphate has been used as a component of culture media, to study its effects as an inhibitor of cluster of differentiation 73 (CD73) and adenosinergic signaling regulation via CD73 or ecto-5′-nucleotidase.

Technology Process of Phosphomethylphosphonic acid adenosyl ester

There total 8 articles about Phosphomethylphosphonic acid adenosyl ester 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: 73.0%

C37H52N6O12P2 → O5'-(dihydroxyphosphorylmethyl-hydroxy-phosphinoyl)-adenosine (3768-14-7)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; for 4h;

DOI:10.1002/anie.201611878

Reference yield: 72.0%

tris(tetrabutylammonium) salt of methylenebis(phosphonic acid) (93978-76-8) + 5'-tosyladenosine (5135-30-8) → O5'-(dihydroxyphosphorylmethyl-hydroxy-phosphinoyl)-adenosine (3768-14-7)

Guidance literature:

In acetonitrile; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(01)90180-7

Reference yield:

2',3'-O-isopropylideneadenosine 5'-methylenebis(phosphonate) disodium salt → O5'-(dihydroxyphosphorylmethyl-hydroxy-phosphinoyl)-adenosine (3768-14-7)

Guidance literature:

With Dowex₅₀WX₈; hydrogen cation; In water; for 24h; Ambient temperature;

DOI:10.1021/jo971859a

upstream raw materials:

α,β-methylene-ATP lithium salt

tris(tetrabutylammonium) salt of methylenebis(phosphonic acid)

5'-tosyladenosine

Downstream raw materials:

adenosine 5'- 5'<*>5'-ester with 2-β-D-ribofuranosyl-4-thiazolecarboxamide

Refernces

• 1、 Engelsma, Sander B.,Meeuwenoord, Nico J.,Overkleeft, Hermen S.,van der Marel, Gijsbert A.,Filippov, Dmitri V.. "Combined Phosphoramidite-Phosphodiester Reagents for the Synthesis of Methylene Bisphosphonates". supporting information. p. 2955 - 2959. Retrieved 2017/03/13.
• 2、 Blackburn, G. Michael,Thatcher, Gregory R. J.,Hosseini, Mir Wais,Lehn, Jean-Marie. "EVIDENCE A FOR PROTOPHOSPHATASE CATALYSED CLEAVAGE OF ADENOSINE TRIPHOSPHATE BY A DISSOCIATIVE-TYPE MECHANISM WITHIN A RECEPTOR-SUBSTRATE COMPLEX". . p. 2779 - 2782. Retrieved 2007/10/02.