(2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid

Base Information

• Chemical Name: (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid
• CAS No.: 4542-23-8
• Molecular Formula: C14H17N5O8
• Molecular Weight: 383.318
• Mol file: 4542-23-8.mol

Synonyms:(2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid;N6-Succinyl Adenosine;

Chemical Property of (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid

Chemical Property:

• Vapor Pressure: 3.44E-28mmHg at 25°C
• Melting Point: >180°C (dec.)
• Boiling Point: 816.4°Cat760mmHg
• Flash Point: 447.6°C
• PSA: 200.15000
• Density: 2.02g/cm³
• LogP: -2.14940
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99%, ^*data from raw suppliers

N6-Succinyl Adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Succinyladenosine (S-Ado) is a biochemical marker of adenylosuccinase deficiency - the genetic defect of purine de novo synthesis. ?S-Ado has been previously reported as normally undetectable in cerebrospinal fluid (CSF) of children not suffering from thi Succinyladenosine (S-Ado) is a biochemical marker of adenylosuccinase deficiency - the genetic defect of purine de novo synthesis. ?S-Ado has been previously reported as normally undetectable in cerebrospinal fluid (CSF) of children not suffering from this defect.

Technology Process of (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid

There total 12 articles about (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid 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:

N-(purine-6-yl)-L-aspartic acid 9-β-D-ribofuranoside-5'-phosphate (19046-78-7) → N-<9-(β-ribofuranosyl)-9H-purin-6-yl>-L-aspartic acid (4542-23-8,30651-34-4,50816-93-8)

Guidance literature:

With human prostate gland;

DOI:10.1021/ja01559a076

Reference yield:

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) → N-<9-(β-ribofuranosyl)-9H-purin-6-yl>-L-aspartic acid (4542-23-8,30651-34-4,50816-93-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / triethylamine / methanol / 0.5 h / Ambient temperature

2: 97 percent / ammonia / methanol / Ambient temperature

3: 84 percent / toluene-4-sulphonic acid monohydrate / tetrahydrofuran / 1 h / 50 °C

4: 88 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 2.5 h / -5 °C

5: 70 percent / N,N-di-isopropylethylamine / N,N-dimethyl-acetamide / 28 h / 70 - 75 °C

6: 0.65 g / aq. formic acid / 3 h / Ambient temperature

7: hydrogen / palladium on carbon / ethanol; acetic acid; H₂O / 2 h

With formic acid; ammonia; hydrogen; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; water; acetic acid;

Reference yield:

6-(4-chlorophenylthio)-9-β-D-ribofuranosyl-9H-purine (132089-81-7) → N-<9-(β-ribofuranosyl)-9H-purin-6-yl>-L-aspartic acid (4542-23-8,30651-34-4,50816-93-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / toluene-4-sulphonic acid monohydrate / tetrahydrofuran / 1 h / 50 °C

2: 88 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 2.5 h / -5 °C

3: 70 percent / N,N-di-isopropylethylamine / N,N-dimethyl-acetamide / 28 h / 70 - 75 °C

4: 0.65 g / aq. formic acid / 3 h / Ambient temperature

5: hydrogen / palladium on carbon / ethanol; acetic acid; H₂O / 2 h

With formic acid; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; water; acetic acid;

upstream raw materials:

6-methylmercaptopurine riboside

aspartic Acid

N-(purine-6-yl)-L-aspartic acid 9-β-D-ribofuranoside-5'-phosphate

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

Downstream raw materials:

acetaldehyde

adenosine

Refernces

• 1、 WHITFELD. "Accumulation of adenine-succinic acid by an adenine-requiring mutant of Neurospora crassa.". . p. 585 - 586. Retrieved 2007/10/07.