Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester

Base Information

• Chemical Name: Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester
• CAS No.: 312710-06-8
• Molecular Formula: C₂₀H₂₅N₆O₁₀P
• Molecular Weight: 540.426

Synonyms:Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester

Chemical Property of Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester

There total 9 articles about Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester 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: 100.0%

3'-O-acetyl-2'-O{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 5'-(2-cyanoethyl methyl phosphate) (312710-16-0) → Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester (312710-06-8)

Guidance literature:

With methylamine; In ethanol; water; at 20 ℃; for 0.333333h;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

Reference yield:

6-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)adenosine (129666-75-7,81246-82-4) → Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester (312710-06-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 36 percent / Bu₂SnCl₂; iPr₂NEt / 1,2-dichloro-ethane / 0.25 h / 80 °C

2: MeNH₂ / ethanol / 0.25 h / 20 °C

3: DMAP / pyridine / 0.5 h / 20 °C

4: 82 percent / CHCl₂COOH / CH₂Cl₂; methanol / 0.33 h / 4 °C

5: 5-(benzylthio)-1H-tetrazole / acetonitrile / 0.33 h / 20 °C

6: I₂ / H₂O; pyridine; tetrahydrofuran

7: 100 percent / MeNH₂ / ethanol; H₂O / 0.33 h / 20 °C

With dichloro-acetic acid; dmap; benzyl tetrazol-5-yl sulphide; dibutyltin chloride; iodine; N-ethyl-N,N-diisopropylamine; methylamine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 1: Condensation / 2: debenzoylation / 3: Acetylation / 4: Hydrolysis / 5: Condensation / 6: Oxidation / 7: Hydrolysis;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

Reference yield:

1-(1-chloromethoxy-ethyl)-2-nitro-benzene → Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester methyl ester (312710-06-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 36 percent / Bu₂SnCl₂; iPr₂NEt / 1,2-dichloro-ethane / 0.25 h / 80 °C

2: MeNH₂ / ethanol / 0.25 h / 20 °C

3: DMAP / pyridine / 0.5 h / 20 °C

4: 82 percent / CHCl₂COOH / CH₂Cl₂; methanol / 0.33 h / 4 °C

5: 5-(benzylthio)-1H-tetrazole / acetonitrile / 0.33 h / 20 °C

6: I₂ / H₂O; pyridine; tetrahydrofuran

7: 100 percent / MeNH₂ / ethanol; H₂O / 0.33 h / 20 °C

With dichloro-acetic acid; dmap; benzyl tetrazol-5-yl sulphide; dibutyltin chloride; iodine; N-ethyl-N,N-diisopropylamine; methylamine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 1: Condensation / 2: debenzoylation / 3: Acetylation / 4: Hydrolysis / 5: Condensation / 6: Oxidation / 7: Hydrolysis;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

upstream raw materials:

3'-O-acetyl-2'-O{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 5'-(2-cyanoethyl methyl phosphate)

2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 5'-(methyl phosphate) 3'-N-{[(2-nitrobenzyl)oxy]carbonyl}-L-phenylalaninate

6-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)adenosine

3'-O-acetyl-2'-O{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine

Downstream raw materials:

2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 3'-{N-[(benzyloxy)carbonyl]-L-phenylalaninate} 5'-(methyl phosphate)

2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 5'-(methyl phosphate) 3'-O-{N-{[(2-nitrobenzyl)oxy]carbonyl}-D-phenylalaninate}

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