N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol

Base Information

• Chemical Name: N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol
• CAS No.: 135042-36-3
• Molecular Formula: C₂₂H₂₉N₇O₃
• Molecular Weight: 439.517
• Mol file: 135042-36-3.mol

Synonyms:N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol

Chemical Property of N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol

There total 12 articles about N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol 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-(N-(benzyloxycarbonyl)-O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol (135042-35-2) → N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol (135042-36-3)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; for 1h; under 760 Torr; Yield given;

DOI:10.1021/jm00113a017

Reference yield:

(2S)-2-[(benzyloxycarbonyl)amino]-3-(4-methoxyphenyl)propanoic acid (17554-34-6) → N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol (135042-36-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N-hydroxysuccinimide, dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT, 25 h

2: glacial acetic acid, H₂ / 10percent Pd/C / 1 h / 760 Torr

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1021/jm00113a017

Reference yield:

(2R,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (77450-03-4) → N-(O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol (135042-36-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 87.7 percent / Et₃N / CH₂Cl₂; tetrahydrofuran / 43 h / Ambient temperature

2: 6.5 percent / triphenylphosphine, DEAD / tetrahydrofuran / 19 h / Ambient temperature

3: 80percent aq. acetic acid / Ambient temperature

4: H₂O / 4 h / Heating

5: trifluoroacetic acid / 1 h / Ambient temperature

6: N-hydroxysuccinimide, dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT, 25 h

7: glacial acetic acid, H₂ / 10percent Pd/C / 1 h / 760 Torr

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a017

upstream raw materials:

N-(N-(benzyloxycarbonyl)-O-methyl-L-tyrosinyl)-cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol

(2S)-2-[(benzyloxycarbonyl)amino]-3-(4-methoxyphenyl)propanoic acid

(2R,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

cis-4-(6-(dimethylamino)-9H-purin-9-yl)-D-prolinol

Refernces