O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

Base Information

Chemical Name:O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate
CAS No.:1352234-62-8
Molecular Formula:C₂₄H₂₆N₄O₆S
Molecular Weight:498.56
Hs Code.:

O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

Synonyms:O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

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Chemical Property of O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

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Technology Process of O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

There total 21 articles about O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate 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: 92.0%

: 1352234-61-7
C₂₀H₂₄N₂O₆

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 1352234-62-8
O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃; for 18h;
DOI:10.1021/jo401166q

Reference yield:

: 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
L-arabinose

: 1352234-62-8
O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

Guidance literature:: Multi-step reaction with 20 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: boron trifluoride 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 / 2 h / 0 - 20 °C

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 23 °C

9.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 6 h / 0 - 23 °C / Molecular sieve

10.1: palladium dichloride; copper diacetate; oxygen / water; N,N-dimethyl acetamide / 48 h

11.1: L-proline / N,N-dimethyl-formamide / 72 h / 20 °C

12.1: tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 4 h / 0 - 20 °C

13.1: dmap / dichloromethane / 24 h / 23 °C

14.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C

15.1: DOWEX 50W-8X ionic exchange resin / water; 1,4-dioxane / 72 h

16.1: pyridine / 16 h / 0 - 20 °C

17.1: acetonitrile / 1 h / 80 °C

17.2: 12 h / 0 - 50 °C

18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C

19.1: methanol; potassium carbonate / 18 h

20.1: dmap / dichloromethane / 18 h / 0 - 20 °C

With pyridine; 1H-imidazole; methanol; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; oxygen; tri-n-butyl-tin hydride; copper diacetate; sodium acetate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; copper(II) sulfate; acetic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 5.1: |Parikh-Doering Oxidation / 6.1: |Sakurai Allylation / 6.2: |Sakurai Allylation / 14.1: |Barton-McCombie Deoxygenation / 17.1: |Vorbrueggen Nucleoside Synthesis / 17.2: |Vorbrueggen Nucleoside Synthesis;
DOI:10.1021/jo401166q

Reference yield:

: 1352234-51-5
1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-β-L-arabinopentodialdofuranose

: 1352234-62-8
O-((2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl) 1H-imidazole-1-carbothioate

Guidance literature:: Multi-step reaction with 15 steps

1.1: boron trifluoride 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 / 2 h / 0 - 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 23 °C

4.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 6 h / 0 - 23 °C / Molecular sieve

5.1: palladium dichloride; copper diacetate; oxygen / water; N,N-dimethyl acetamide / 48 h

6.1: L-proline / N,N-dimethyl-formamide / 72 h / 20 °C

7.1: tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 4 h / 0 - 20 °C

8.1: dmap / dichloromethane / 24 h / 23 °C

9.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C

10.1: DOWEX 50W-8X ionic exchange resin / water; 1,4-dioxane / 72 h

11.1: pyridine / 16 h / 0 - 20 °C

12.1: acetonitrile / 1 h / 80 °C

12.2: 12 h / 0 - 50 °C

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C

14.1: methanol; potassium carbonate / 18 h

15.1: dmap / dichloromethane / 18 h / 0 - 20 °C

With pyridine; methanol; dmap; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; oxygen; tri-n-butyl-tin hydride; copper diacetate; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 1.1: |Sakurai Allylation / 1.2: |Sakurai Allylation / 9.1: |Barton-McCombie Deoxygenation / 12.1: |Vorbrueggen Nucleoside Synthesis / 12.2: |Vorbrueggen Nucleoside Synthesis;
DOI:10.1021/jo401166q