(S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid

Base Information

• Chemical Name: (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid
• CAS No.: 1341220-51-6
• Molecular Formula: C₂₁H₂₆N₆O₅S
• Molecular Weight: 474.541
• Mol file: 1341220-51-6.mol

Synonyms:(S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid

Chemical Property of (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid

There total 8 articles about (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid 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: 52.9%

(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(chloromethyl)tetrahydrofuran-3-ol (1341220-44-7) + L-homocysteine thiolactone hydrochloride (31828-68-9) → (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid (1341220-51-6)

Guidance literature:

L-homocysteine thiolactone hydrochloride; With sodium hydroxide; In water; at 100 ℃; for 1.5h; Inert atmosphere;

(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(chloromethyl)tetrahydrofuran-3-ol; With potassium iodide; at 100 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jm201000j

Reference yield:

phenyldiazomethane (908094-04-2) → (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid (1341220-51-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tin(II) chloride dihdyrate / methanol; 1,2-dimethoxyethane / 25 °C / Inert atmosphere

1.2: 5 h / 25 °C

2.1: sodium hydroxide / water / 1.5 h / 100 °C / Inert atmosphere

2.2: 16 h / 100 °C / Inert atmosphere

With tin(II) chloride dihdyrate; sodium hydroxide; In methanol; 1,2-dimethoxyethane; water;

DOI:10.1021/jm201000j

Reference yield:

N-benzyl-p-toluenesulfonamide (1576-37-0) → (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid (1341220-51-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium nitrite / acetic anhydride; acetic acid / 0 - 25 °C

2.1: sodium methylate / methanol; diethyl ether / 0.5 h / Reflux

3.1: tin(II) chloride dihdyrate / methanol; 1,2-dimethoxyethane / 25 °C / Inert atmosphere

3.2: 5 h / 25 °C

4.1: sodium hydroxide / water / 1.5 h / 100 °C / Inert atmosphere

4.2: 16 h / 100 °C / Inert atmosphere

With tin(II) chloride dihdyrate; sodium methylate; sodium hydroxide; sodium nitrite; In methanol; 1,2-dimethoxyethane; diethyl ether; water; acetic anhydride; acetic acid;

DOI:10.1021/jm201000j

upstream raw materials:

(E)-N'-(9-((2R,3R,4S,5S)-5-(chloromethyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-6yl)-N,N-dimethylformimidamide

(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(chloromethyl)tetrahydrofuran-3-ol

L-homocysteine thiolactone hydrochloride

N-nitroso-N-benzyl-p-toluenesulphonamide

Downstream raw materials:

3'-benzyl-S-adenosylmethionine iodide

Refernces