methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Base Information

• Chemical Name: methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
• CAS No.: 261909-26-6
• Molecular Formula: C₂₄H₃₀N₇O₅P
• Molecular Weight: 527.52
• Mol file: 261909-26-6.mol

Synonyms:methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Chemical Property of methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

There total 4 articles about methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate 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: 76.0%

C13H18ClN2O5P + abacavir (136470-78-5,128131-83-9,136470-79-6) → methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate (261909-26-6)

Guidance literature:

abacavir; With tert-butylmagnesium chloride; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

C₁₃H₁₈ClN₂O₅P; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1039/c8cc04708a

Reference yield:

abacavir (136470-78-5,128131-83-9,136470-79-6) + phenyl methoxyalaninyl phosphorochloridate (142629-80-9) → methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate (261909-26-6)

Guidance literature:

With tert-butylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 70h;

DOI:10.1021/jm0491400

Reference yield:

O-phenyl phosphorodichloridate (770-12-7) → methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate (261909-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / -80 - 20 °C

2: 442 mg / t-BuMgCl / tetrahydrofuran / 70 h / 20 °C

With tert-butylmagnesium chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0491400

upstream raw materials:

abacavir

phenyl methoxyalaninyl phosphorochloridate

O-phenyl phosphorodichloridate

Refernces

• 1、 -. "CYCLOPENTENYL PURINE DERIVATIVE OR SALT THEREOF". Paragraph 0469-0474. . Retrieved 2021/05/28.