dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine

Base Information

• Chemical Name: dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine
• CAS No.: 87990-06-5
• Molecular Formula: C₃₀H₃₅N₇O₆
• Molecular Weight: 589.651
• Mol file: 87990-06-5.mol

Synonyms:

Chemical Property of dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine

There total 14 articles about dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine 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:

desoxy-4-α et β-D,L-threo-pentopyranose (20072-97-3,33428-78-3,75800-66-7,75800-68-9,78854-43-0,89919-60-8,126638-07-1,126638-08-2) → dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine (87990-06-5,87990-07-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / pyridine / 12 h / Ambient temperature

2: acetyl chloride / diethyl ether / 24 h / 4 °C

3: 100 percent / HgCN, molecular sieve 3 A / nitromethane / 3 h / Heating

4: 69 percent / methanol / 48 h / Ambient temperature

5: 91 percent / pyridine / 5 h / 0 °C

6: 73 percent / NaN₃ / dimethylformamide / 24 h / 100 °C

7: 97 percent / NaOH / methanol / 5 h / 50 - 60 °C

8: 95 percent / hydrogen / 10 percent Pd on carbon / methanol / 20 h / 760 Torr / Ambient temperature

9: hexafluorophosphate de benzotriazol-1-yl-oxy-tris(dimethylamino) phosphonium, diisopropylethylamine, molecular sieve 3 A / dimethylformamide / 20 h / Ambient temperature

With pyridine; sodium hydroxide; sodium azide; 3 A molecular sieve; hydrogen; Quecksilber(I)-cyanid; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; acetyl chloride; palladium on activated charcoal; In methanol; diethyl ether; nitromethane; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570200338

Reference yield:

Acetic acid (3S,4R)-4-acetoxy-2-chloro-tetrahydro-pyran-3-yl ester (87990-00-9) → dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine (87990-06-5,87990-07-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / HgCN, molecular sieve 3 A / nitromethane / 3 h / Heating

2: 69 percent / methanol / 48 h / Ambient temperature

3: 91 percent / pyridine / 5 h / 0 °C

4: 73 percent / NaN₃ / dimethylformamide / 24 h / 100 °C

5: 97 percent / NaOH / methanol / 5 h / 50 - 60 °C

6: 95 percent / hydrogen / 10 percent Pd on carbon / methanol / 20 h / 760 Torr / Ambient temperature

7: hexafluorophosphate de benzotriazol-1-yl-oxy-tris(dimethylamino) phosphonium, diisopropylethylamine, molecular sieve 3 A / dimethylformamide / 20 h / Ambient temperature

With pyridine; sodium hydroxide; sodium azide; 3 A molecular sieve; hydrogen; Quecksilber(I)-cyanid; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; nitromethane; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570200338

Reference yield:

dimethylamino-6-(desoxy-4'-α-D,L-threo-pentopyranosyl)-9-purine (87990-02-1) → dimethylamino-6-(N-benzyloxycarbonyl-p-methoxyphenyl-L-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine (87990-06-5,87990-07-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / pyridine / 5 h / 0 °C

2: 73 percent / NaN₃ / dimethylformamide / 24 h / 100 °C

3: 97 percent / NaOH / methanol / 5 h / 50 - 60 °C

4: 95 percent / hydrogen / 10 percent Pd on carbon / methanol / 20 h / 760 Torr / Ambient temperature

5: hexafluorophosphate de benzotriazol-1-yl-oxy-tris(dimethylamino) phosphonium, diisopropylethylamine, molecular sieve 3 A / dimethylformamide / 20 h / Ambient temperature

With pyridine; sodium hydroxide; sodium azide; 3 A molecular sieve; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570200338

upstream raw materials:

desoxy-4-α et β-D,L-threo-pentopyranose

Acetic acid (3S,4R)-4-acetoxy-2-chloro-tetrahydro-pyran-3-yl ester

trifluoroacetamido-3-didesoxy-3,4-β-D,L-erythro-pentopyranoside de methyle

dimethylamino-6-(desoxy-4'-α-D,L-threo-pentopyranosyl)-9-purine

Downstream raw materials:

dimethylamino-6-(p-methoxyphenyl-N-alanylamino-3'-didesoxy-3',4'-β-D,L-erythro-pentopyranosyl)-9-purine

Refernces