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

Base Information

Chemical Name:2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate
CAS No.:1276114-21-6
Molecular Formula:C₂₇H₂₇Cl₃N₄O₈
Molecular Weight:641.892
Hs Code.:

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

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

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

There total 5 articles about 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate 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: 85.0%

: 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levuniloyl-α/β-D-glucopyranose

: 545-06-2
trichloroacetonitrile

: 1276114-21-6
2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: In dichloromethane; for 2h; Molecular sieve;
DOI:10.1021/jo400467g

Reference yield:

: 138889-14-2
2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

: 1276114-21-6
2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 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

4: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C

5: dichloromethane / 2 h / Molecular sieve

With dmap; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; ethanethiol; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo400467g

Reference yield:

: 120312-08-5
2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

: 1276114-21-6
2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

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

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C

4: dichloromethane / 2 h / Molecular sieve

With dmap; tetrabutyl ammonium fluoride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo400467g