(S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester

Base Information

• Chemical Name: (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester
• CAS No.: 517877-41-7
• Molecular Formula: C₂₁H₂₅ClN₆O₄
• Molecular Weight: 460.92
• Mol file: 517877-41-7.mol

Synonyms:(S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester

Chemical Property of (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester

There total 2 articles about (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl 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: 34.0%

benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate (79069-16-2) + 2-Amino-6-chloropurin (10310-21-1) → (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester (517877-41-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In acetonitrile; at -20 - 0 ℃; for 264h;

DOI:10.1002/1522-2675(200211)85:11<3855::AID-HLCA3855>3.0.CO;2-A

Reference yield:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester (517877-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tBuOCOCl; NEM / tetrahydrofuran

1.2: 95 percent / NaBH₄ / methanol

2.1: 34 percent / DEAD; PPh₃ / acetonitrile / 264 h / -20 - 0 °C

With N-Ethylmaleimide; tert-butyl chloroformate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; acetonitrile; 2.1: Mitsunobu reaction;

DOI:10.1002/1522-2675(200211)85:11<3855::AID-HLCA3855>3.0.CO;2-A

Reference yield: 59.0%

(S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester (517877-41-7) → (S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine (517877-42-8) + (S)-N-[(tert-butoxy)carbonyl]-γ-(O6-benzylguanin-9-yl)-β-homoalanine

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 50 ℃; for 20h;

DOI:10.1002/1522-2675(200211)85:11<3855::AID-HLCA3855>3.0.CO;2-A

upstream raw materials:

benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate

2-Amino-6-chloropurin

BOC-L-aspartic acid 4-benzyl ester

Downstream raw materials:

(S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine

Refernces