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

Base Information

• Chemical Name: 6-(4-bromobenzyloxy)-3-deoxy-1,2-O-isopropylidene-D-glucose
• CAS No.: 724733-47-5
• Molecular Formula: C₁₆H₂₁BrO₅
• Molecular Weight: 373.244
• Mol file: 724733-47-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 6-(4-bromobenzyloxy)-3-deoxy-1,2-O-isopropylidene-D-glucose 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: 100.0%

3-deoxy-1,2-O-isopropylidene-D-glucose (4005-46-3,4494-96-6,22248-87-9,142941-40-0) + 1-bromomethyl-4-bromobenzene (589-15-1) → 6-(4-bromobenzyloxy)-3-deoxy-1,2-O-isopropylidene-D-glucose (724733-47-5)

Guidance literature:

3-deoxy-1,2-O-isopropylidene-D-glucose; With di(n-butyl)tin oxide; In toluene; for 5h; Heating;

1-bromomethyl-4-bromobenzene; With tetrabutylammomium bromide; In toluene; at 90 ℃;

DOI:10.1021/jm031106i

Reference yield: 68.0%

6-(4-bromobenzyloxy)-3-deoxy-1,2-O-isopropylidene-D-glucose (724733-47-5) → 5-azido-3,5-dideoxy-6-O-(4-bromobenzyl)-1,2-O-isopropylidene-L-lyxo-hexofuranose (724733-49-7)

Guidance literature:

6-(4-bromobenzyloxy)-3-deoxy-1,2-O-isopropylidene-D-glucose; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -15 - 0 ℃;

With diphenyl phosphoryl azide; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield:

6-(4-bromobenzyloxy)-3-deoxy-1,2-O-isopropylidene-D-glucose (724733-47-5) → 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 (724733-56-6)

Guidance literature:

Multi-step reaction with 5 steps

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

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

2.1: aq. acetic acid / 1 h / Heating

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

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

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

4.1: acetyl chloride / 48 h / 20 °C

With sodium periodate; di-isopropyl azodicarboxylate; acetic acid; acetyl chloride; triphenylphosphine; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1021/jm031106i

upstream raw materials:

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

1-bromomethyl-4-bromobenzene

Downstream raw materials:

5-azido-3,5-dideoxy-6-O-(4-bromobenzyl)-1,2-O-isopropylidene-L-lyxo-hexofuranose

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

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)-3-cyclohexylcarbamoyl-2-hydroxy-propyl]-2,4,6-trifluoro-benzamide