4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

Base Information

• Chemical Name: 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal
• CAS No.: 1590392-16-7
• Molecular Formula: C₄₄H₅₆N₂O₁₄S
• Molecular Weight: 869
• Mol file: 1590392-16-7.mol

Synonyms:4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

Chemical Property of 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

There total 9 articles about 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal 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: 83.0%

4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal (1590392-15-6) + N,N`-sulfuryldiimidazole (7189-69-7) → 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal (1590392-16-7)

Guidance literature:

4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

N,N`-sulfuryldiimidazole; In N,N-dimethyl-formamide; mineral oil; at -30 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.carres.2014.01.020

Reference yield:

4-O-(3,4,6-tri-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal (1590392-14-5) → 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal (1590392-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 1 h / -30 °C / Inert atmosphere

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.carres.2014.01.020

Reference yield:

4-O-(3,6-di-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal (1590392-13-4) → 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal (1590392-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

1.2: 12 h / 0 - 20 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: 1 h / -30 °C / Inert atmosphere

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.carres.2014.01.020

upstream raw materials:

4-O-(6-O-benzyl-3,4-O-isopropylidene-2-O-p-methoxybenzyl-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

4-O-(3,6-di-O-benzyl-4-deoxy-2-O-p-methoxybenzyl-β-D-erhytrohex-4-enopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

4-O-(3,6-di-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

4-O-(3,4,6-tri-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

Downstream raw materials:

4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal