2-CHLORO-2',3'-O-ISOPROPYLIDENEADENOSINE-5'-N-ETHYLCARBOXAMIDE

Base Information

• Chemical Name: 2-CHLORO-2',3'-O-ISOPROPYLIDENEADENOSINE-5'-N-ETHYLCARBOXAMIDE
• CAS No.: 120225-75-4
• Molecular Formula: C15H19 Cl N6 O4
• Molecular Weight: 382.8
• Mol file: 120225-75-4.mol

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

Chemical Property of 2-CHLORO-2',3'-O-ISOPROPYLIDENEADENOSINE-5'-N-ETHYLCARBOXAMIDE

Chemical Property:

• Melting Point: 210-212掳C
• PSA: 126.41000
• LogP: 1.58760
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO, MeOH, DMF; 50 mg/L gives a clear colourless solution

Purity/Quality:

97% ^*data from raw suppliers

2-Chloro-2’,3’-O-isopropylideneadenosine-5’-N-ethylcarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A potent selective adenosine receptor agonist 2-Chloro-2’,3’-O-isopropylideneadenosine-5’-N-ethylcarboxamide is a potent and selective adenosine receptor agonist (1). It is also used to prepare photoreactive 2-?phenethylamine derivatives (2).

Technology Process of 2-CHLORO-2',3'-O-ISOPROPYLIDENEADENOSINE-5'-N-ETHYLCARBOXAMIDE

There total 4 articles about 2-CHLORO-2',3'-O-ISOPROPYLIDENEADENOSINE-5'-N-ETHYLCARBOXAMIDE 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:

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (24639-06-3) → 2-chloro-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide (120225-75-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / aq. KOH, KMnO₄ / H₂O / 72 h

2: SOCl₂ / dimethylformamide / 2 h / 50 °C

3: CH₂Cl₂ / 1 h / Ambient temperature

With potassium hydroxide; potassium permanganate; thionyl chloride; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00169a015

Reference yield:

2-Chloroadenosine (146-77-0) → 2-chloro-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide (120225-75-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / camphorsulfonic acid / acetone / 16 h / Ambient temperature

2: 74 percent / aq. KOH, KMnO₄ / H₂O / 72 h

3: SOCl₂ / dimethylformamide / 2 h / 50 °C

4: CH₂Cl₂ / 1 h / Ambient temperature

With potassium hydroxide; potassium permanganate; thionyl chloride; camphor-10-sulfonic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00169a015

Reference yield:

2-chloro-2',3'-O-isopropylideneadenosine-5'-carboxylic acid (72209-19-9) → 2-chloro-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide (120225-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / dimethylformamide / 2 h / 50 °C

2: CH₂Cl₂ / 1 h / Ambient temperature

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00169a015

upstream raw materials:

ethylamine

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

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

2-Chloroadenosine

Downstream raw materials:

(3aS,4S,6R,6aR)-6-{6-Amino-2-[2-(4-fluoro-phenyl)-ethylamino]-purin-9-yl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

(4-{2-[6-Amino-9-((3aR,4R,6S,6aS)-6-ethylcarbamoyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-2-ylamino]-ethyl}-phenyl)-acetic acid tert-butyl ester

(4-{2-[6-Amino-9-((3aR,4R,6S,6aS)-6-ethylcarbamoyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-2-ylamino]-ethyl}-phenoxy)-acetic acid tert-butyl ester

2-(2-phenyl)ethylamino-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide

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