Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 1053614-01-9
• Molecular Formula: C₁₆H₁₉N₃O₉S
• Molecular Weight: 429.408

Synonyms:Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester 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:

1-β-D-glucopyranosyl-2-nitroimidazole (83107-46-4) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester (1053614-01-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/jm00011a013

Reference yield:

1-(2'-nitroimidazolyl)-β-2,3,4,6-tetra-O-acetyl-D-glucose (67774-11-2) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester (1053614-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. Et₃N / methanol / 1.5 h / 20 °C

2: pyridine / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jm00011a013

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (6919-96-6) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-nitro-imidazol-1-yl)-tetrahydro-pyran-2-ylmethyl ester (1053614-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide / 0.5 h / 60 - 70 °C

2: aq. Et₃N / methanol / 1.5 h / 20 °C

3: pyridine / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; potassium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00011a013

upstream raw materials:

1-β-D-glucopyranosyl-2-nitroimidazole

p-toluenesulfonyl chloride

1-(2'-nitroimidazolyl)-β-2,3,4,6-tetra-O-acetyl-D-glucose

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

2-nitro-1H-<6-tosyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyl>imidazole

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