(3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

Base Information

Chemical Name:(3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
CAS No.:368878-56-2
Molecular Formula:C₁₅H₁₉N₅O₇S
Molecular Weight:413.411
Hs Code.:

Synonyms:(3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

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Chemical Property of (3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

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Technology Process of (3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

There total 10 articles about (3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol 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: 70.0%

: 368878-42-6
2-O-acetyl-6-azido-1,6-dideoxy-3,4-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)mannojirimycin

: 368878-56-2
(3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(01)00650-0

Reference yield:

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 368878-56-2
(3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

Guidance literature:: Multi-step reaction with 8 steps

1: Na₂CO₃ / CH₂Cl₂; H₂O / 1 h / 20 °C

2: 14.13 g / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 74 percent / NaH / tetrahydrofuran / 4 h / 20 °C

4: 98 percent / NaN₃ / dimethylformamide / 8 h / 90 °C

5: Dowex 50X₈-200 / methanol; H₂O / 48 h / 20 °C

6: 0.68 g / PPh₃; CBr₄ / tetrahydrofuran / 0.5 h / 20 °C

7: 76 percent / Et₃N; DMAP / CH₂Cl₂ / 96 h / 20 °C

8: 70 percent / K₂CO₃ / methanol / 2 h / 20 °C

With pyridine; dmap; sodium azide; carbon tetrabromide; Dowex 50X₈-200; sodium hydride; sodium carbonate; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00650-0

Reference yield:

: 368878-38-0
1-azido-1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)amino-D-mannitol

: 368878-56-2
(3aR,4R,7R,7aR)-4-Azidomethyl-2,2-dimethyl-5-(4-nitro-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

Guidance literature:: Multi-step reaction with 4 steps

1: Dowex 50X₈-200 / methanol; H₂O / 48 h / 20 °C

2: 0.68 g / PPh₃; CBr₄ / tetrahydrofuran / 0.5 h / 20 °C

3: 76 percent / Et₃N; DMAP / CH₂Cl₂ / 96 h / 20 °C

4: 70 percent / K₂CO₃ / methanol / 2 h / 20 °C

With dmap; carbon tetrabromide; Dowex 50X₈-200; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)00650-0