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

Base Information

Chemical Name:(2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl acetate
CAS No.:1453105-11-7
Molecular Formula:C₂₂H₂₆N₂O₇
Molecular Weight:430.458
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 19 articles about (2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl acetate 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: 83.0%

: 1352234-60-6
C₂₅H₃₄N₂O₇Si

: 1453105-11-7
(2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl acetate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 0.5h;
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

: 1453105-11-7
(2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl acetate

Guidance literature:: Multi-step reaction with 18 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

With pyridine; 1H-imidazole; 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; 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

: 1453105-11-7
(2R,3R,3aS,7S,7aS)-7-(benzyloxy)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)octahydrobenzofuran-3-yl acetate

Guidance literature:: Multi-step reaction with 13 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

With pyridine; 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; 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