(3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol

Base Information

• Chemical Name: (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol
• CAS No.: 1426415-10-2
• Molecular Formula: C₁₆H₁₈N₂O₉
• Molecular Weight: 382.327
• Mol file: 1426415-10-2.mol

Synonyms:(3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol

Chemical Property of (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol

There total 10 articles about (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol 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: 50.0%

(3S,4R,6S)-6-hydroxymethyl-3,4-O-isopropylidenetetrahydro-2H-pyran-3,4-diol (1426415-09-9) + 3,5-dinitrobenoyl chloride (99-33-2) → (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol (1426415-10-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.3998/ark.5550190.0014.209

Reference yield:

C12H18O6 (1200835-08-0) → (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol (1426415-10-2)

Guidance literature:

Multi-step reaction with 9 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 20 °C

2: 1H-imidazole / 4 h / -15 - 20 °C / Inert atmosphere

3: toluene / 1 h / Reflux

4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / Reflux; Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6: pyridine / dichloromethane / 3 h / 20 °C / Inert atmosphere

7: zinc(II) nitrate hexahydrate / acetonitrile / 12 h / 20 °C

8: sodium hydride / tetrahydrofuran / 2 h / 20 °C

9: triethylamine / dichloromethane / 6 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; zinc(II) nitrate hexahydrate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.3998/ark.5550190.0014.209

Reference yield:

1-O-(tert-butyldiphenyl)silyl-4-O-(1H-imidazol-1ylmethanethionyl)2,3:5,6-di-O-isopropylidene-D-gulitol → (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol (1426415-10-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / Reflux; Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3: pyridine / dichloromethane / 3 h / 20 °C / Inert atmosphere

4: zinc(II) nitrate hexahydrate / acetonitrile / 12 h / 20 °C

5: sodium hydride / tetrahydrofuran / 2 h / 20 °C

6: triethylamine / dichloromethane / 6 h / 20 °C / Inert atmosphere

With pyridine; zinc(II) nitrate hexahydrate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.3998/ark.5550190.0014.209

upstream raw materials:

D-gulonic acid-δ-lactone

(3S,4R,6S)-6-hydroxymethyl-3,4-O-isopropylidenetetrahydro-2H-pyran-3,4-diol

3,5-dinitrobenoyl chloride

C₁₂H₁₈O₆