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

Base Information

• Chemical Name: 2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 3'-{N-[(benzyloxy)carbonyl]-L-phenylalaninate} 5'-(methyl phosphate)
• CAS No.: 312710-20-6
• Molecular Formula: C₃₇H₄₀N₇O₁₃P
• Molecular Weight: 821.737

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 9 articles about 2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 3'-{N-[(benzyloxy)carbonyl]-L-phenylalaninate} 5'-(methyl phosphate) 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: 52.0%

N-Cbz-L-Phe (1161-13-3) + 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) → 2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 3'-{N-[(benzyloxy)carbonyl]-L-phenylalaninate} 5'-(methyl phosphate) (312710-20-6)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-pyrrolidin-1-ylpyridine; N-ethyl-N,N-diisopropylamine; In pyridine; at 20 ℃;

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) → 2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 3'-{N-[(benzyloxy)carbonyl]-L-phenylalaninate} 5'-(methyl phosphate) (312710-20-6)

Guidance literature:

Multi-step reaction with 8 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

8: 52 percent / iPr₂NEt; 4-(pyrrolidin-1-yl)pyridine; BOP / pyridine / 20 °C

With dichloro-acetic acid; dmap; benzyl tetrazol-5-yl sulphide; dibutyltin chloride; iodine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-pyrrolidin-1-ylpyridine; 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 / 8: Condensation;

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 → 2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}adenosine 3'-{N-[(benzyloxy)carbonyl]-L-phenylalaninate} 5'-(methyl phosphate) (312710-20-6)

Guidance literature:

Multi-step reaction with 8 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

8: 52 percent / iPr₂NEt; 4-(pyrrolidin-1-yl)pyridine; BOP / pyridine / 20 °C

With dichloro-acetic acid; dmap; benzyl tetrazol-5-yl sulphide; dibutyltin chloride; iodine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-pyrrolidin-1-ylpyridine; 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 / 8: Condensation;

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

upstream raw materials:

N-Cbz-L-Phe

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

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

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

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