3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

Base Information

Chemical Name:3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose
CAS No.:1458119-02-2
Molecular Formula:C₁₇H₂₂N₄O₆
Molecular Weight:378.385
Hs Code.:

Synonyms:3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

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Chemical Property of 3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

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Technology Process of 3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

There total 5 articles about 3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose 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: 90.0%

: 1458119-01-1
3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

: 1458119-02-2
3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

Guidance literature:: With acetic acid; at 50 ℃; for 3h;
DOI:10.1039/c3ob41462k

Reference yield:

: 689218-40-4
(3S)-3-C-azido-3-C-carboxy-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexose

: 1458119-02-2
3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 20 °C / Molecular sieve; Inert atmosphere

2.1: acetic acid / 3 h / 50 °C

With benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1039/c3ob41462k

Reference yield:

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 1458119-02-2
3-azido-3-deoxy-1,2-O-isopropylidene-3-C-benzylcarbamoyl-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 3.3 h / -78 °C / Inert atmosphere

2.1: sodium azide; tetra-(n-butyl)ammonium iodide; sodium hydroxide / 1,4-dioxane; water / 1 h / 20 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 20 °C / Molecular sieve; Inert atmosphere

4.1: acetic acid / 3 h / 50 °C

With sodium azide; tetra-(n-butyl)ammonium iodide; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1039/c3ob41462k