(3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one

Base Information

Chemical Name:(3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one
CAS No.:1328893-60-2
Molecular Formula:C₂₀H₂₃N₃O₁₁
Molecular Weight:481.416
Hs Code.:

Synonyms:(3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one

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Chemical Property of (3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one

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Technology Process of (3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one

There total 4 articles about (3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one 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: 77.0%

: 1161856-07-0
(5R,6R,8R,9R,4'R)-6-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-8,9-dimethylmethylenedioxy-1,7-dioxa-3-azaspiro[4.4]nonan-2-one

: 70-34-8,65727-75-5
2,4-Dinitrofluorobenzene

: 1328893-60-2
(3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one

Guidance literature:: (5R,6R,8R,9R,4'R)-6-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-8,9-dimethylmethylenedioxy-1,7-dioxa-3-azaspiro[4.4]nonan-2-one; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

2,4-Dinitrofluorobenzene; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 1.16667h; Inert atmosphere;
DOI:10.1016/j.carres.2013.04.008

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 1328893-60-2
(3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / water; dichloromethane / 0.58 h / -10 - 0 °C / pH 9.5 / Alkaline conditions; Large scale

1.2: 2.5 h / 0 - 20 °C / Large scale

2.1: palladium 10% on activated carbon / tetrahydrofuran; methanol / 17 h / 40 °C / 22801.5 Torr

3.1: triethylamine / tetrahydrofuran / 3 h / -5 - 20 °C

4.1: sodium hydride; 1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-glucofuranose / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere

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

5.2: 1.17 h / 0 - 20 °C / Inert atmosphere

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-glucofuranose; palladium 10% on activated carbon; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.carres.2013.04.008

Reference yield:

: 1,2; 5,6-di-O-isopropylidene-3-C-[[[(phenylmethoxy)carbonyl]amino]methyl]-α-D-allofuranose

: 1328893-60-2
(3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride; 1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-glucofuranose / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere

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

2.2: 1.17 h / 0 - 20 °C / Inert atmosphere

With 1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-glucofuranose; sodium hydride; In N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.carres.2013.04.008