(3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:1380778-65-3
Molecular Formula:C₁₇H₁₈N₄O₄
Molecular Weight:342.354
Hs Code.:

Synonyms:(3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 5 articles about (3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 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: 75.0%

: 1380778-62-0
(3aR,5R,6S,6aR)-5-ethynyl-6-methylamino-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 34897-85-3
o-azidobenzoyl chloride

: 1380778-65-3
(3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 8h; Inert atmosphere;
DOI:10.1021/jo3004327

Reference yield:

: 16848-19-4,24384-84-7,71165-01-0,71187-80-9,73881-34-2,91067-83-3
3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 1380778-65-3
(3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethylamine / dichloromethane / 2 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C

2.2: 6 h / 0 - 20 °C

3.1: acetic acid / water / 25 °C

4.1: sodium periodate / methanol; water / 0.75 h / 0 °C

5.1: potassium carbonate / methanol / 12 h / 20 °C

6.1: potassium carbonate; thiophenol / acetonitrile / 3 h / 20 °C

7.1: triethylamine / dichloromethane / 8 h / 0 °C / Inert atmosphere

With sodium periodate; sodium hydride; potassium carbonate; acetic acid; thiophenol; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo3004327

Reference yield:

: 1380778-59-5
3-deoxy-3-(N-4-nitrobenzenesulfonyl-N-methylamino)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 1380778-65-3
(3aR,5R,6S,6aR)-6-(2-azidobenzoyl)methylamino-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 5 steps

1: acetic acid / water / 25 °C

2: sodium periodate / methanol; water / 0.75 h / 0 °C

3: potassium carbonate / methanol / 12 h / 20 °C

4: potassium carbonate; thiophenol / acetonitrile / 3 h / 20 °C

5: triethylamine / dichloromethane / 8 h / 0 °C / Inert atmosphere

With sodium periodate; potassium carbonate; acetic acid; thiophenol; triethylamine; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo3004327