2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole

Base Information

• Chemical Name: 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole
• CAS No.: 1320161-42-9
• Molecular Formula: C₃₇H₂₉ClN₂O₁₀
• Molecular Weight: 697.098

Synonyms:2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole

Chemical Property of 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole

Chemical Property:

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Technology Process of 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole

There total 2 articles about 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole 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: 96.0%

5-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)tetrazole (706784-62-5) + chloroacetyl chloride (79-04-9) → 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole (1320161-42-9)

Guidance literature:

In toluene; for 2h; Reflux;

DOI:10.1016/j.carres.2011.03.004

Reference yield:

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide (286369-05-9) → 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole (1320161-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: azido tributyltin (IV) / diethylene glycol dimethyl ether / 26 h / Reflux

2: toluene / 2 h / Reflux

With azido tributyltin (IV); In diethylene glycol dimethyl ether; toluene;

DOI:10.1016/j.carres.2011.03.004

Reference yield: 90.0%

2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole (1320161-42-9) → 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-azidomethyl-1,3,4-oxadiazole (1320161-43-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1016/j.carres.2011.03.004

upstream raw materials:

5-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)tetrazole

chloroacetyl chloride

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide

Downstream raw materials:

2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-azidomethyl-1,3,4-oxadiazole

2-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-5-(4'-phenyl-1',2',3'-triazol-1'-methyl)-1,3,4-oxadiazole

2-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-5-(4'-ethoxycarbonyl-1',2',3'-triazol-1'-methyl)-1,3,4-oxadiazole

2-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-5-(4'-hydroxymethyl-1',2',3'-triazol-1'-methyl)-1,3,4-oxadiazole

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