1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol

Base Information

• Chemical Name: 1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol
• CAS No.: 368878-36-8
• Molecular Formula: C₁₉H₂₈N₂O₁₁S₂
• Molecular Weight: 524.57

Synonyms:1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol

Chemical Property of 1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol

Chemical Property:

Purity/Quality:

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Technology Process of 1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol

There total 2 articles about 1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol 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:

methanesulfonyl chloride (124-63-0) + N-[(S)-2-Hydroxy-2-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-4-nitro-benzenesulfonamide → 1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol (368878-36-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00650-0

Reference yield:

4-Nitrobenzenesulfonyl chloride (98-74-8) → 1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol (368878-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂CO₃ / CH₂Cl₂; H₂O / 1 h / 20 °C

2: 14.13 g / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; sodium carbonate; In dichloromethane; water;

DOI:10.1016/S0040-4020(01)00650-0

Reference yield: 74.0%

1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-nitrobenzenesulfonyl)amino-D-glucitol (368878-36-8) → 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1,2-(N-p-nitrobenzenesulfonyl)imino-D-mannitol (368878-37-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(01)00650-0

upstream raw materials:

methanesulfonyl chloride

4-Nitrobenzenesulfonyl chloride

Downstream raw materials:

1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1,2-(N-p-nitrobenzenesulfonyl)imino-D-mannitol

6-phenylthio-1,6-dideoxy-3,4-O-isopropylidene-mannojirimycin

(3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

1-azido-6-bromo-3,4-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)amino-1,2,6-trideoxy-D-mannitol

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