(S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester

Base Information

• Chemical Name: (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester
• CAS No.: 1064684-24-7
• Molecular Formula: C₂₂H₂₈BrFN₃O₉P
• Molecular Weight: 608.355
• Mol file: 1064684-24-7.mol

Synonyms:(S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester

Chemical Property of (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester

There total 4 articles about (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl 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: 26.0%

2'-deoxy-2'-fluoro-2'-methyluridine (863329-66-2,2041584-99-8) + 4-bromophenyl methoxy-valyl phosphorochloridate (1064685-41-1) → (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester (1064684-24-7)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran; at 20 ℃;

Reference yield:

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate (817204-32-3) → (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester (1064684-24-7)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / water / Reflux

2: methanol; ammonia / 0 - 20 °C

3: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C

With 1-methyl-1H-imidazole; methanol; ammonia; acetic acid; In tetrahydrofuran; water;

Reference yield:

(2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine (817204-33-4) → (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester (1064684-24-7)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 1.67 h / 0 °C / Inert atmosphere

2: acetic acid / water / Reflux

3: methanol; ammonia / 0 - 20 °C

4: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C

With pyridine; 1-methyl-1H-imidazole; methanol; ammonia; acetic acid; In tetrahydrofuran; water;

upstream raw materials:

2'-deoxy-2'-fluoro-2'-methyluridine

4-bromophenyl methoxy-valyl phosphorochloridate

(2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Refernces