(S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate

Base Information

• Chemical Name: (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate
• CAS No.: 1333389-23-3
• Molecular Formula: C₁₉H₂₀N₈O₅
• Molecular Weight: 440.418
• Mol file: 1333389-23-3.mol

Synonyms:

Chemical Property of (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate

There total 3 articles about (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate 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:

(S)-cyanomethyl 2-azido-3-phenylpropanoate (1333389-08-4) → (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate (1333389-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutylammonium acetate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 12 h

2: chlorotriisopropylsilane; trifluoroacetic acid / 24 h

With chlorotriisopropylsilane; tetrabutylammonium acetate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja2055098

Reference yield:

(2S)-2-azido-3-phenylpropanoic acid (79410-35-8) → (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate (1333389-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / 12 h

2: tetrabutylammonium acetate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 12 h

3: chlorotriisopropylsilane; trifluoroacetic acid / 24 h

With chlorotriisopropylsilane; tetrabutylammonium acetate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja2055098

Reference yield:

(S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-3-yl 2-azido-3-phenylpropanoate (1333389-17-5) → (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-azido-3-phenylpropanoate (1333389-23-3)

Guidance literature:

With chlorotriisopropylsilane; trifluoroacetic acid; for 24h;

DOI:10.1021/ja2055098

upstream raw materials:

(S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-3-yl 2-azido-3-phenylpropanoate

(S)-cyanomethyl 2-azido-3-phenylpropanoate

(2S)-2-azido-3-phenylpropanoic acid

Downstream raw materials:

PheLysAlaAcm