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

Base Information

• Chemical Name: 6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylo-hexofuranos-5-ulose
• CAS No.: 1384188-39-9
• Molecular Formula: C₁₇H₂₁BrO₆
• Molecular Weight: 401.254
• Mol file: 1384188-39-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylo-hexofuranos-5-ulose 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: 82.5%

6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-glucofuranose (1384188-37-7) → 6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylo-hexofuranos-5-ulose (1384188-39-9)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; for 4h; Reflux;

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) → 6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylo-hexofuranos-5-ulose (1384188-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / methanol / 24 h

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

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

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

DOI:10.1016/j.carres.2012.04.011

Reference yield: 87.2%

6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylo-hexofuranos-5-ulose (1384188-39-9) + N,N'-bis[(dimethylamino)methylene]thiourea (96818-59-6) → 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)

Guidance literature:

6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-xylo-hexofuranos-5-ulose; N,N'-bis[(dimethylamino)methylene]thiourea; In dichloromethane; for 3h; Reflux; Inert atmosphere;

With triethylamine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

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-glucofuranose

1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

Downstream raw materials:

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

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

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

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