(3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic acid methyl ester

Base Information

• Chemical Name: (3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic acid methyl ester
• CAS No.: 724733-51-1
• Molecular Formula: C₁₃H₁₆BrN₃O₄
• Molecular Weight: 358.192
• Mol file: 724733-51-1.mol

Synonyms:

Chemical Property of (3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic acid methyl ester

There total 6 articles about (3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic 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:

3-deoxy-1,2-O-isopropylidene-D-glucose (4005-46-3,4494-96-6,22248-87-9,142941-40-0) → (3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic acid methyl ester (724733-51-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dibutyl tin oxide / toluene / 5 h / Heating

1.2: 100 percent / tetrabutylammonium bromide / toluene / 90 °C

2.1: triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -15 °C

2.2: diphenylphosphoryl azide / tetrahydrofuran / 0 - 20 °C

3.1: aq. acetic acid / 1 h / Heating

4.1: aq. sodium periodate / 2-methyl-propan-2-ol / 0.25 h / 20 °C

4.2: aq. sodium periodate / 2-methyl-propan-2-ol / 0.25 h / 20 °C

4.3: aq. sodium hydroxide / dioxane / 1 h / 20 °C

5.1: acetyl chloride / 48 h / 20 °C

With sodium periodate; di-isopropyl azodicarboxylate; di(n-butyl)tin oxide; acetic acid; acetyl chloride; triphenylphosphine; In tetrahydrofuran; toluene; tert-butyl alcohol;

DOI:10.1021/jm031106i

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) → (3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic acid methyl ester (724733-51-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dibutyl tin oxide / toluene / 5 h / Heating

1.2: 100 percent / tetrabutylammonium bromide / toluene / 90 °C

2.1: triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -15 °C

2.2: diphenylphosphoryl azide / tetrahydrofuran / 0 - 20 °C

3.1: aq. acetic acid / 1 h / Heating

4.1: aq. sodium periodate / 2-methyl-propan-2-ol / 0.25 h / 20 °C

4.2: aq. sodium periodate / 2-methyl-propan-2-ol / 0.25 h / 20 °C

4.3: aq. sodium hydroxide / dioxane / 1 h / 20 °C

5.1: acetyl chloride / 48 h / 20 °C

With sodium periodate; di-isopropyl azodicarboxylate; di(n-butyl)tin oxide; acetic acid; acetyl chloride; triphenylphosphine; In tetrahydrofuran; toluene; tert-butyl alcohol;

DOI:10.1021/jm031106i

Reference yield:

(2S,3R,5S)-5-[(S)-1-Azido-2-(4-bromo-benzyloxy)-ethyl]-tetrahydro-furan-2,3-diol → (3S,4S)-4-azido-5-(4-bromobenzyloxy)-3-hydroxypentanoic acid methyl ester (724733-51-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. sodium periodate / 2-methyl-propan-2-ol / 0.25 h / 20 °C

1.2: aq. sodium periodate / 2-methyl-propan-2-ol / 0.25 h / 20 °C

1.3: aq. sodium hydroxide / dioxane / 1 h / 20 °C

2.1: acetyl chloride / 48 h / 20 °C

With sodium periodate; acetyl chloride; In tert-butyl alcohol;

DOI:10.1021/jm031106i

upstream raw materials:

methanol

3-deoxy-1,2-O-isopropylidene-D-glucose

1-bromomethyl-4-bromobenzene

6-(4-bromobenzyloxy)-3-deoxy-1,2-O-isopropylidene-D-glucose

Downstream raw materials:

N-{(1S,2S)-1-(4-Bromo-benzyloxymethyl)-3-[(S)-1-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-ethylcarbamoyl]-2-hydroxy-propyl}-2,4,6-trifluoro-benzamide

Pyridine-2-carboxylic acid ((S)-1-{(1S,2S)-1-(4-bromo-benzyloxymethyl)-3-[(S)-1-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-ethylcarbamoyl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide

Pyridine-2-carboxylic acid {(S)-1-[(1S,2S)-1-(4-bromo-benzyloxymethyl)-3-butylcarbamoyl-2-hydroxy-propylcarbamoyl]-2-methyl-propyl}-amide

N-{(1S,2S)-1-(4-Bromo-benzyloxymethyl)-2-hydroxy-3-[2-(3-methoxy-phenyl)-ethylcarbamoyl]-propyl}-2,4,6-trifluoro-benzamide