[(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide

Base Information

• Chemical Name: [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide
• CAS No.: 86467-70-1
• Molecular Formula: C₁₉H₂₄N₂O₈
• Molecular Weight: 408.408

Synonyms:[(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide

Chemical Property of [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide

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Technology Process of [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide

There total 2 articles about [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide 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%

2,3:5,6-di-O-isopropylidene-D-mannose oxime (35023-80-4) + 4-nitrobenzaldehdye (555-16-8) → [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide (86467-70-1)

Guidance literature:

In toluene; for 24h; Heating;

DOI:10.1002/anie.200461934

Reference yield:

2,3:5,6-di-O-isopropylidene-D-mannose oxime (35023-80-4) + 4-nitrobenzaldehdye (555-16-8) → 2,3;5,6-di-O-isopropylidene-D-mannose oxime (83258-84-8,99395-01-4,104012-86-4,136598-86-2) + [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide (86467-70-1)

Guidance literature:

In dichloromethane; for 30h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1002/hlca.19830660310

Reference yield: 84.0%

4-Nitrophenyl isocyanate (100-28-7) + [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl][(4-nitrophenyl)meth-(Z)-ylidene]amine N-oxide (86467-70-1) → (R)-2-[(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3,4-bis(4-nitrophenyl)-1,2,4-oxadiazolidin-5-one + (S)-2-[(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3,4-bis(4-nitrophenyl)-1,2,4-oxadiazolidin-5-one

Guidance literature:

In dichloromethane; at 23 ℃; for 19h;

DOI:10.1002/anie.200461934

upstream raw materials:

2,3:5,6-di-O-isopropylidene-D-mannose oxime

4-nitrobenzaldehdye

Downstream raw materials:

(R)-4-benzoyl-2-[(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-(4-nitrophenyl)-1,2,4-oxadiazolidin-5-one

(R)-2-[(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-(4-nitrophenyl)-1,2,4-oxadiazolidin-5-one

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