1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

Base Information

Chemical Name:1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione
CAS No.:1373612-96-4
Molecular Formula:C₂₅H₂₆N₂O₆
Molecular Weight:450.491
Hs Code.:

Synonyms:1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

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Chemical Property of 1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

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Technology Process of 1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

There total 9 articles about 1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione 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: 59.0%

: 1373612-94-2
3,5-di(benzyloxy)-2-(4-methylphenylsulfonyloxymethyl)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan

: 66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6
uracil

: 1373612-96-4
1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

Guidance literature:: uracil; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 90 ℃; for 0.25h;

3,5-di(benzyloxy)-2-(4-methylphenylsulfonyloxymethyl)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan; In N,N-dimethyl-formamide; mineral oil; at 90 ℃; for 3h;
DOI:10.1016/j.carres.2012.01.018

Reference yield:

: 1373612-88-4
2,2-dimethyl-4-(4-methylphenylsulfonyloxymethyl)-6-vinyl-(3aR,4S,6aS)-perhydrofuro[3,4-d][1,3]dioxole

: 1373612-96-4
1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfuric acid; water / 1,4-dioxane / 2 h / 80 °C

2.1: oxygen; copper(l) chloride; palladium dichloride / water; N,N-dimethyl-formamide / 4 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / Cooling

3.2: 1 h / 0 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 90 °C

4.2: 3 h / 90 °C

With sulfuric acid; water; oxygen; sodium hydride; copper(l) chloride; palladium dichloride; In 1,4-dioxane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.carres.2012.01.018

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 1373612-96-4
1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 0.5 h / 10 °C

1.2: 10 - 20 °C

2.1: pyridine; dmap / 3.5 h / 0 - 20 °C

3.1: bismuth(III) chloride / dichloromethane / 2 h / 20 °C

4.1: 1H-imidazole; iodine; triphenylphosphine / toluene / Heating

5.1: sulfuric acid; water / 1,4-dioxane / 2 h / 80 °C

6.1: oxygen; copper(l) chloride; palladium dichloride / water; N,N-dimethyl-formamide / 4 h / 20 °C

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / Cooling

7.2: 1 h / 0 °C

8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 90 °C

8.2: 3 h / 90 °C

With pyridine; 1H-imidazole; dmap; bismuth(III) chloride; sulfuric acid; potassium tert-butylate; water; iodine; oxygen; sodium hydride; triphenylphosphine; copper(l) chloride; palladium dichloride; In 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1016/j.carres.2012.01.018