5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione

Base Information

• Chemical Name: 5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione
• CAS No.: 58459-25-9
• Molecular Formula: C₂₂H₂₄N₂O₉S₂
• Molecular Weight: 524.573

Synonyms:5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione

Chemical Property of 5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione

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Technology Process of 5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione

There total 3 articles about 5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione 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:

5-phenyl-1,3,4-thiadiazol-2-yl 2,3,4,6,-tetra-O-acetyl-1-thio-β-D-glucopyranoside (58459-24-8) → 5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione (58459-25-9)

Guidance literature:

With mercury dibromide; In toluene; Heating;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (6919-96-6) → 5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione (58459-25-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / acetone

2: HgBr₂ / toluene / Heating

With sodium hydroxide; mercury dibromide; In acetone; toluene;

Reference yield:

2-phenyl-1,3,4-thiadiazole-5(4H)-thione (5585-19-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 5-phenyl-1,3,4-thiadiazol-2-yl 2,3,4,6,-tetra-O-acetyl-1-thio-β-D-glucopyranoside (58459-24-8) + 5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazole-2-thione (58459-25-9)

Guidance literature:

With potassium hydroxide; In water; acetone; for 5h; Ambient temperature;

DOI:10.1016/S0008-6215(00)83296-6

upstream raw materials:

5-phenyl-1,3,4-thiadiazol-2-yl 2,3,4,6,-tetra-O-acetyl-1-thio-β-D-glucopyranoside

2-phenyl-1,3,4-thiadiazole-5(4H)-thione

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

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

Downstream raw materials:

3-β-D-glucopyranosyl-5-phenyl-3H-[1,3,4]thiadiazole-2-thione

5-phenyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)-3H-[1,3,4]thiadiazol-2-one

3-β-D-glucopyranosyl-5-phenyl-3H-[1,3,4]thiadiazol-2-one

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