1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 1453105-13-9
• Molecular Formula: C₂₀H₂₄N₂O₆
• Molecular Weight: 388.42

Synonyms:1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property of 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

There total 17 articles about 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 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: 99.0%

C22H24N2O7 (1352234-73-1) → 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (1453105-13-9)

Guidance literature:

With potassium carbonate; In methanol; for 6h;

DOI:10.1021/jo401166q

Reference yield:

1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-β-L-arabinopentodialdofuranose (1352234-51-5) → 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (1453105-13-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: magnesium bromide diethyl etherate / dichloromethane / 0.08 h / -78 °C

1.2: 3 h / 78 °C

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h

4.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 3 h / 0 - 20 °C

5.1: tetrahydrofuran / 0.17 h / 0 °C

6.1: DOWEX 50W-8X ionic exchange resin / water; 1,4-dioxane / 48 h

7.1: pyridine / 16 h / 0 - 20 °C

8.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 80 °C

8.2: 12 h / 0 - 50 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.33 h / 40 °C

11.1: potassium carbonate / methanol / 6 h

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N,O-bis-(trimethylsilyl)-acetamide; magnesium bromide diethyl etherate; tetrabutyl ammonium fluoride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 1.1: |Sakurai Allylation / 1.2: |Sakurai Allylation / 8.1: |Vorbrueggen Nucleoside Synthesis / 8.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/jo401166q

Reference yield:

L-arabinose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (1453105-13-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 60 °C

2.1: copper(II) sulfate; sulfuric acid / 1 h / 23 °C

3.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 23 °C

5.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide; dichloromethane / 0.17 h / -20 °C

6.1: magnesium bromide diethyl etherate / dichloromethane / 0.08 h / -78 °C

6.2: 3 h / 78 °C

7.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h

9.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 3 h / 0 - 20 °C

10.1: tetrahydrofuran / 0.17 h / 0 °C

11.1: DOWEX 50W-8X ionic exchange resin / water; 1,4-dioxane / 48 h

12.1: pyridine / 16 h / 0 - 20 °C

13.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 80 °C

13.2: 12 h / 0 - 50 °C

14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

15.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.33 h / 40 °C

16.1: potassium carbonate / methanol / 6 h

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N,O-bis-(trimethylsilyl)-acetamide; magnesium bromide diethyl etherate; sulfuric acid; tetrabutyl ammonium fluoride; sodium acetate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; mineral oil; 5.1: |Parikh-Doering Oxidation / 6.1: |Sakurai Allylation / 6.2: |Sakurai Allylation / 13.1: |Vorbrueggen Nucleoside Synthesis / 13.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/jo401166q

upstream raw materials:

1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-β-L-arabinopentodialdofuranose

1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-6-deoxy-6-C-vinyl-α-D-galactofuranose

1,2-O-isopropylidene-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

L-arabinose

Downstream raw materials:

1-((2R,3aS,7R,7aS)-7-(benzyloxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2R,3aS,7R,7aS)-7-(bis(4-methoxyphenyl)(phenyl)methoxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

(2R,3aS,7R,7aS)-7-(bis(4-methoxyphenyl)(phenyl)methoxy)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-hexahydrobenzofuran-3a(4H)-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite

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