2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSYL AZIDE

Base Information

• Chemical Name: 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSYL AZIDE
• CAS No.: 80887-27-0
• Molecular Formula: C22H24 N4 O5
• Molecular Weight: 426.47
• Mol file: 80887-27-0.mol

Synonyms:Pyrano[3,2-d]-1,3-dioxin,b-D-glucopyranosyl azide deriv.

Chemical Property of 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSYL AZIDE

Chemical Property:

• PSA: 115.77000
• LogP: 3.00166
• Storage Temp.: Freezer
• Solubility.: very faint turbidity in Pyridine

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosylAzide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl Azide (CAS# 80887-27-0) can be used in the synthesis and molecular modelling conformational analysis of N,N'',N''''-triacetylchitotriose pseudosugar analogs. It is also useful in the visible-light-mediated regioselective green preparation of triazoles via iridium-catalyzed photocycloaddition of azides with alkynes.

Technology Process of 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSYL AZIDE

There total 3 articles about 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSYL AZIDE 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: 82.0%

benzyl bromide (100-39-0) + 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (35521-01-8,168397-51-1) → 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (80887-27-0)

Guidance literature:

With barium hydroxide octahydrate; barium(II) oxide; In N,N-dimethyl-formamide; for 2h; Ambient temperature; 1.) N,N-dimethylformamide, RT, 2 h, 2.) chloroform, reflux, 2 h;

DOI:10.1246/bcsj.54.3570

Reference yield:

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide (29847-23-2) → 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (80887-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / formic acid / 0.5 h / Ambient temperature

2: 82 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 2 h / Ambient temperature; 1.) N,N-dimethylformamide, RT, 2 h, 2.) chloroform, reflux, 2 h

With formic acid; barium hydroxide octahydrate; barium(II) oxide; In N,N-dimethyl-formamide;

DOI:10.1246/bcsj.54.3570

Reference yield:

benzaldehyde (100-52-7) → 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (80887-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / formic acid / 0.5 h / Ambient temperature

2: 82 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 2 h / Ambient temperature; 1.) N,N-dimethylformamide, RT, 2 h, 2.) chloroform, reflux, 2 h

With formic acid; barium hydroxide octahydrate; barium(II) oxide; In N,N-dimethyl-formamide;

DOI:10.1246/bcsj.54.3570

upstream raw materials:

benzyl bromide

2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide

benzaldehyde

Downstream raw materials:

2-acetamido-3,6-di-O-benzyl-4-O-succinoyl-2-deoxy-β-D-glucopyranosyl azide

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

Refernces