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

Base Information

Chemical Name:2-O-acetyl-6-azido-1,6-dideoxy-3,4-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)mannojirimycin
CAS No.:368878-42-6
Molecular Formula:C₁₇H₂₁N₅O₈S
Molecular Weight:455.448
Hs Code.:

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

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Chemical Property of 2-O-acetyl-6-azido-1,6-dideoxy-3,4-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)mannojirimycin

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Technology Process of 2-O-acetyl-6-azido-1,6-dideoxy-3,4-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)mannojirimycin

There total 9 articles about 2-O-acetyl-6-azido-1,6-dideoxy-3,4-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)mannojirimycin 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: 76.0%

: 108-24-7
acetic anhydride

: 368878-40-4
1-azido-6-bromo-3,4-O-isopropylidene-2-(N-p-nitrobenzenesulfonyl)amino-1,2,6-trideoxy-D-mannitol

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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 96h;
DOI:10.1016/S0040-4020(01)00650-0

Reference yield: 70.0%

: 368878-54-0
Acetic acid (S)-1-{(4S,5R)-5-[(R)-2-azido-1-(4-nitro-benzenesulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-iodo-ethyl ester

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

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 72h;
DOI:10.1016/S0040-4020(01)00650-0

Reference yield:

: 98-74-8
4-Nitrobenzenesulfonyl chloride

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

Guidance literature:: Multi-step reaction with 7 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

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