Ethyl adenosine-5'-carboxylate

Base Information

• Chemical Name: Ethyl adenosine-5'-carboxylate
• CAS No.: 35803-57-7
• Molecular Formula: C12H15 N5 O5
• Molecular Weight: 309.282
• UNII: H90LD92T80
• DSSTox Substance ID: DTXSID60957187
• Nikkaji Number: J264.824E
• ChEMBL ID: CHEMBL5073759
• Mol file: 35803-57-7.mol

Synonyms:Abbott 40557;Abbott 40557, hydrochloride;Abbott 40557, mono-hydrochloride;adenosine-5'-carboxylic acid ethyl ester;ethyl adenosine-5'-carboxylate;MY 201

Chemical Property of Ethyl adenosine-5'-carboxylate

Chemical Property:

• Vapor Pressure: 1.26E-19mmHg at 25°C
• Refractive Index: 1.788
• Boiling Point: 619.5°Cat760mmHg
• Flash Point: 328.5°C
• PSA: 145.61000
• Density: 1.86g/cm³
• LogP: -0.82800
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 309.10731860
• Heavy Atom Count: 22
• Complexity: 427

Purity/Quality:

97% ^*data from raw suppliers

ETHYL ADENOSINE-5'-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl adenosine-5'-carboxylate

There total 4 articles about Ethyl adenosine-5'-carboxylate 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: 86.0%

ethanol (64-17-5) + adenosine 5'-carboxylic acid (3415-09-6) → ethyl adenosine-5'-carboxylate (35803-57-7)

Guidance literature:

With thionyl chloride; at 5 - 10 ℃; for 18h;

DOI:10.1021/jm00159a020

Reference yield:

2',3'-isopropylidene adenosine (362-75-4) → ethyl adenosine-5'-carboxylate (35803-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / KMnO₄, 80percent aq. AcOH / Ambient temperature

2: 55 percent / aq. HCl / 0.5 h / 70 °C

3: 86 percent / SOCl₂ / 18 h / 5 - 10 °C

With hydrogenchloride; potassium permanganate; thionyl chloride; acetic acid;

DOI:10.1021/jm00159a020

Reference yield:

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → ethyl adenosine-5'-carboxylate (35803-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / aq. HCl / 0.5 h / 70 °C

2: 86 percent / SOCl₂ / 18 h / 5 - 10 °C

With hydrogenchloride; thionyl chloride;

DOI:10.1021/jm00159a020

upstream raw materials:

ethanol

adenosine 5'-carboxylic acid

2',3'-isopropylidene adenosine

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

Downstream raw materials:

N⁶-acetyladenine

(2S,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid (2-hydroxy-3-m-tolyloxy-propyl)-amide

5'-N-Ethylcarboxamidoadenosine

Refernces

• 1、 Olsson,Kusachi,Thompson,Ukena,Padgett,Daly. "N6-substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors.". . p. 1683 - 1689. Retrieved 2007/10/02.