2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose

Base Information

• Chemical Name: 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose
• CAS No.: 1447801-83-3
• Molecular Formula: C₃₁H₄₁N₃O₈Si
• Molecular Weight: 611.767

Synonyms:2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose

Chemical Property of 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose

There total 2 articles about 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose 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: 91.0%

2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (1447801-82-2) + levulinic acid (123-76-2) → 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose (1447801-83-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo400467g

Reference yield:

2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (138889-14-2) → 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose (1447801-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanethiol; toluene-4-sulfonic acid / dichloromethane / 3 h / 20 °C

2: triethylamine / acetonitrile / 11 h / -40 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

With dmap; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; ethanethiol; In dichloromethane; acetonitrile;

DOI:10.1021/jo400467g

Reference yield:

2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose (1447801-83-3) → 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levuniloyl-α/β-D-glucopyranose

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jo400467g

upstream raw materials:

2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

levulinic acid

Downstream raw materials:

2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

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