5'-ETHYLCARBOXAMIDO-2',3'-ISOPROPYLIDENEADENOSINE

Base Information

• Chemical Name: 5'-ETHYLCARBOXAMIDO-2',3'-ISOPROPYLIDENEADENOSINE
• CAS No.: 39491-53-7
• Molecular Formula: C15H20 N6 O4
• Molecular Weight: 362.38
• Mol file: 39491-53-7.mol

Synonyms:Furo[3,4-d]-1,3-dioxole,b-D-ribofuranuronamide deriv.

Chemical Property of 5'-ETHYLCARBOXAMIDO-2',3'-ISOPROPYLIDENEADENOSINE

Chemical Property:

• Melting Point: 200-202°C
• Refractive Index: 1.758
• PSA: 129.90000
• Density: 1.692g/cm³
• LogP: 1.38360
• Solubility.: DMSO, Ethanol, Methanol

Purity/Quality:

97% ^*data from raw suppliers

5’-Ethylcarboxamido-2’,3’-isopropylideneAdenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: As a useful template for the development of A2B adenosine receptor agonists, 5'-EthylcarboxaMido-2',3'-isopropylidene Adenosine was confirmed to be a full agonist in a functional assay based on the measurement of its capacity to modulate cAMP levels in CHO cells expressing the hA2B receptor. A useful template for the development of A2B adenosine receptor agonists. It was confirmed to be a full agonist in a functional assay based on the measurement of its capacity to modulate cAMP levels in CHO cells expressing the hA2B receptor.

Technology Process of 5'-ETHYLCARBOXAMIDO-2',3'-ISOPROPYLIDENEADENOSINE

There total 6 articles about 5'-ETHYLCARBOXAMIDO-2',3'-ISOPROPYLIDENEADENOSINE 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: 72.0%

ethylamine (75-04-7,85404-22-4) + 2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → 5'-N-ethyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-53-7)

Guidance literature:

With Isopropenyl chloroformate; triethylamine; In water; N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

DOI:10.1021/jm9804984

Reference yield:

ethylamine (75-04-7,85404-22-4) + 2',3'-O-isopropylideneadenosine-5'-carbonyl chloride (39491-49-1) → 5'-N-ethyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-53-7)

Guidance literature:

at -60 - -40 ℃; for 2h; Yield given;

DOI:10.1021/jm00177a021

Reference yield:

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → 5'-N-ethyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-53-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: dimethylformamide / 1 h / 20 °C

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

DOI:10.1021/jm000150k

upstream raw materials:

ethylamine

2',3'-O-isopropylideneadenosine-5'-carbonyl chloride

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

(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester

Downstream raw materials:

1-deoxy-1-[6-[[[(4-(cyclohexylaminosulfonyl)phenyl)amino]carbonyl]amino]-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide

1-deoxy-1-[6-[[[(4-((4-methoxyphenyl)aminosulfonyl)phenyl)amino]carbonyl]amino]-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide

1-deoxy-1-[6-[[[(4-(bis-2-chloroethylaminosulfonyl)phenyl)amino]carbonyl]amino]-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide

1-deoxy-1-[6-[[[(4-(benzylaminosulfonyl)phenyl)amino]carbonyl]amino]-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide

Refernces

• 1、 Umino,Yoshioka,Saitoh,Minakawa,Nakata,Matsuda. "Nucleosides and nucleotides. 200. Reinvestigation of 5′-N-ethylcarboxamidoadenosine derivatives: Structure-activity relationships for P3 purinoceptor-like proteins". . p. 208 - 214. Retrieved 2007/10/03.
• 2、 Prasad, Raj Nandan,Bariana, Dilbagh S.,Fung, Anthony,Savic, Milica,Tietje, Karin,et al.. "Modification of the 5' Position of Purine Nucleosides. 2. Synthesis and Some Cardiovascular Properties of Adenosine-5'-(N-substituted)carboxamides". . p. 313 - 319. Retrieved 2007/10/02.