5'-N-methylcarboxamidoadenosine

Base Information

• Chemical Name: 5'-N-methylcarboxamidoadenosine
• CAS No.: 35788-27-3
• Molecular Formula: C₁₁H₁₄N₆O₄
• Molecular Weight: 294.27
• DSSTox Substance ID: DTXSID101168111
• Nikkaji Number: J452.999E
• Wikidata: Q76009734
• Pharos Ligand ID: G9AYAXK6PBK9
• ChEMBL ID: CHEMBL519809
• Mol file: 35788-27-3.mol

Synonyms:5'-N-methylcarboxamideadenosine;MECA

Chemical Property of 5'-N-methylcarboxamidoadenosine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 148.41000
• Density: 1.98g/cm³
• LogP: -1.25420
• Solubility.: 0.1 M HCl: soluble
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 294.10765295
• Heavy Atom Count: 21
• Complexity: 412

Purity/Quality:

99% ^*data from raw suppliers

5'-N-METHYLCARBOXAMIDOADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O

Technology Process of 5'-N-methylcarboxamidoadenosine

There total 8 articles about 5'-N-methylcarboxamidoadenosine 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: 69.0%

methyl 1-[adenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate (89177-37-7) + methylamine (74-89-5) → 5'-N-methylcarboxamidoadenosine (35788-27-3)

Guidance literature:

In tetrahydrofuran; at 110 ℃; for 0.333333h; microwave irradiation;

DOI:10.1016/j.tet.2007.11.100

Reference yield: 43.0%

5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-51-5) → 5'-N-methylcarboxamidoadenosine (35788-27-3)

Guidance literature:

With trifluoroacetic acid; for 0.5h; Ambient temperature;

DOI:10.1021/jm9804984

Reference yield:

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → 5'-N-methylcarboxamidoadenosine (35788-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 3 h / 20 °C

2: dimethylformamide / 1 h / 20 °C

3: 80percent aq. TFA / 20 °C

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1021/jm000150k

upstream raw materials:

adenosine 5'-(N-methyl)carbonyl chloride

methylamine

5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine

2',3'-isopropylideneadenosine-5'-carboxylic acid

Downstream raw materials:

N⁶-(3-iodobenzyl)adenosine-5'-N-methyluronamide

Refernces

• 1、 Devine, Shane M.,Scammells, Peter J.. "An efficient convergent synthesis of adenosine-5′-N-alkyluronamides". . p. 1772 - 1777. Retrieved 2008/09/18.
• 2、 Wnuk, Stanislaw F.,Liu, Siming,Yuan, Chong-Sheng,Borchardt, Ronald T.,Robins, Morris J.. "Inactivation of S-adenosyl-L-homocysteine hydrolase by amide and ester derivatives of adenosine-5'-carboxylic acid". . p. 4162 - 4166. Retrieved 2007/10/03.