N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide

Base Information

• Chemical Name: N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide
• CAS No.: 1385026-75-4
• Molecular Formula: C₄₀H₃₁N₃O₁₅S
• Molecular Weight: 825.763

Synonyms:N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide

Chemical Property of N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide

Chemical Property:

Purity/Quality:

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Technology Process of N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide

There total 4 articles about N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide 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: 44.0%

2,4-dinitrobenzenesulfonyl chloride (1656-44-6) + (2R,3R,4S,5R,6R)-2-amino-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (41093-31-6,108967-44-8,115969-98-7,33639-91-7) → N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide (1385026-75-4)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1080/07328303.2012.663431

Reference yield:

D-glucopyranosyl azide (20379-59-3) → N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide (1385026-75-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 14.5 h / 0 - 20 °C / Inert atmosphere

2: platinum(IV) oxide; hydrogen / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

3: pyridine; dmap / 1 h / 20 °C / Inert atmosphere

With pyridine; dmap; platinum(IV) oxide; hydrogen; In ethyl acetate;

DOI:10.1080/07328303.2012.663431

Reference yield:

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1) → N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide (1385026-75-4)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; sodium / 1.5 h / 20 °C / Inert atmosphere

2: pyridine / 14.5 h / 0 - 20 °C / Inert atmosphere

3: platinum(IV) oxide; hydrogen / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

4: pyridine; dmap / 1 h / 20 °C / Inert atmosphere

With pyridine; methanol; dmap; platinum(IV) oxide; hydrogen; sodium; In ethyl acetate;

DOI:10.1080/07328303.2012.663431

upstream raw materials:

N-Methoxy-N-methyl (1,2,3,4-Di-O-isopropylidene-D-galactopyranose uronic acid) amide

D-glucopyranosyl azide

2,4-dinitrobenzenesulfonyl chloride

(2R,3R,4S,5R,6R)-2-amino-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Downstream raw materials:

(2R,3R,4S,5R,6R)-2-acetamido-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

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