N6-Methyladenosine-5'-monophosphate

Base Information

• Chemical Name: N6-Methyladenosine-5'-monophosphate
• CAS No.: 4229-50-9
• Molecular Formula: C11H16N5O7P
• Molecular Weight: 361.251
• ChEMBL ID: CHEMBL1230507
• DSSTox Substance ID: DTXSID60587882
• Metabolomics Workbench ID: 56370
• Nikkaji Number: J710.068J
• Wikidata: Q27120391
• Mol file: 4229-50-9.mol

Synonyms:4229-50-9;N(6)-methyl-AMP;N6-METHYLADENOSINE-5'-MONOPHOSPHATE;N-methyladenosine 5'-(dihydrogen phosphate);CHEMBL1230507;N(6)-methyl-5'-adenylic acid;CHEBI:40196;N(6)-methyl-[5']adenylic acid;N(6)-methyl-5'-phosphoadenosine;N(6)-methyladenosine 5'-monophosphate;((2R,3S,4R,5R)-3,4-Dihydroxy-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate;N-Methyl-5'-adenylic acid;CHEMBL609083;SCHEMBL4307198;n6-methyl-adenosine monophosphate;DTXSID60587882;{[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(methylamino)-9H-purin-9-yl]oxolan-2-yl]methoxy}phosphonic acid;BDBM50367106;NCGC00163320-01;PD045691;Q27120391

Chemical Property of N6-Methyladenosine-5'-monophosphate

Chemical Property:

• XLogP3: -2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 361.07873486
• Heavy Atom Count: 24
• Complexity: 495

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O
• Isomeric SMILES: CNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O

Technology Process of N6-Methyladenosine-5'-monophosphate

There total 9 articles about N6-Methyladenosine-5'-monophosphate 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: 51.0%

triethyl phosphate (78-40-0) + N6-methyladenosine (1867-73-8) → N6-methyl AMP (4229-50-9,49717-66-0) + C11H17N5O10P2 (1359697-50-9)

Guidance literature:

With water; trichlorophosphate; at 0 ℃;

DOI:10.1021/jm201127y

Reference yield:

N6-methyladenosine (1867-73-8) → N6-methyl AMP (4229-50-9,49717-66-0)

Guidance literature:

With triethyl phosphate; water; trichlorophosphate; at 0 ℃; for 2h;

DOI:10.1021/jm900728u

Reference yield:

C11H14Cl2N5O5P → N6-methyl AMP (4229-50-9,49717-66-0) + N6-Methyl-ATP (3130-39-0)

Guidance literature:

With tributyl-amine; bis(tri-n-butylammonium) pyrophosphate; In N,N-dimethyl-formamide; at -15 ℃; for 2h;

DOI:10.1080/15257771003709569

upstream raw materials:

N⁶-methyladenosine

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

6-N-methyladenosine 5'-acetate

triethyl phosphate

Downstream raw materials:

5'-inosine monophosphate

Refernces

• 1、 Gillerman, Irina,Fischer, Bilha. "An improved one-pot synthesis of nucleoside 5'-triphosphate analogues". experimental part. p. 245 - 256. Retrieved 2011/08/06.