3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole

Base Information

• Chemical Name: 3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole
• CAS No.: 1384188-50-4
• Molecular Formula: C₂₈H₂₅BrN₂O₇S
• Molecular Weight: 613.486
• Mol file: 1384188-50-4.mol

Synonyms:3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole

Chemical Property of 3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole

There total 5 articles about 3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole 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: 86.9%

N,N-dimethylformamidyl-5-(1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylofuranos-5-ulo-5-yl)-1,3-thiazole (1384188-46-8) + para-bromophenacyl bromide (99-73-0,132309-76-3) → 3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole (1384188-50-4)

Guidance literature:

N,N-dimethylformamidyl-5-(1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylofuranos-5-ulo-5-yl)-1,3-thiazole; para-bromophenacyl bromide; In tetrahydrofuran; at 100 ℃; for 1.5h; Microwave irradiation;

With triethylamine; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/j.carres.2012.04.011

Reference yield:

1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose (109536-51-8,142226-16-2,69940-04-1) → 3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole (1384188-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide; triphenylphosphine / N,N-dimethyl-formamide / 3.5 h / 20 °C / Cooling with ice; Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 4 h / Reflux

3.1: dichloromethane / 3 h / Reflux; Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 1.5 h / 100 °C / Microwave irradiation

4.2: 16 h / 20 °C

With N-Bromosuccinimide; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2012.04.011

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose (115693-78-2,142226-15-1,69940-02-9) → 3-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)-5-(p-bromobenzoyl)imidazo[2,1-b]thiazole (1384188-50-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sulfuric acid / methanol / 24 h

2.1: N-Bromosuccinimide; triphenylphosphine / N,N-dimethyl-formamide / 3.5 h / 20 °C / Cooling with ice; Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 4 h / Reflux

4.1: dichloromethane / 3 h / Reflux; Inert atmosphere

4.2: 12 h / 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 1.5 h / 100 °C / Microwave irradiation

5.2: 16 h / 20 °C

With N-Bromosuccinimide; sulfuric acid; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2012.04.011

upstream raw materials:

6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylo-hexofuranos-5-ulose

N,N-dimethylformamidyl-5-(1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylofuranos-5-ulo-5-yl)-1,3-thiazole

para-bromophenacyl bromide

6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-glucofuranose

Downstream raw materials:

5-(p-bromobenzoyl)-3-(α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

5-(p-bromobenzoyl)-3-(β-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole