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

Base Information

Chemical Name:1-((2R,3aR,7S,7aS)-7-(benzyloxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
CAS No.:1352234-63-9
Molecular Formula:C₂₀H₂₄N₂O₅
Molecular Weight:372.421
Hs Code.:

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

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

Chemical Property:

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

There total 28 articles about 1-((2R,3aR,7S,7aS)-7-(benzyloxy)-3a-hydroxyoctahydrobenzofuran-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: 80.0%

: 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

: 1352234-63-9
1-((2R,3aR,7S,7aS)-7-(benzyloxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 23 - 110 ℃; for 0.5h;
DOI:10.1021/jo401166q

Reference yield:

: 103763-12-8,103763-13-9
5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose

: 1352234-63-9
1-((2R,3aR,7S,7aS)-7-(benzyloxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:: Multi-step reaction with 14 steps

1.1: copper(II) sulfate / sulfuric acid

2.1: sodium hydride; tetrabutyl ammonium fluoride / N,N-dimethyl-formamide; tetrahydrofuran

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran

4.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide; pyridine / dichloromethane; dimethyl sulfoxide

5.1: boron trifluoride diethyl etherate / dichloromethane / -78 °C

6.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane

8.1: pyridinium chlorochromate

9.1: L-proline

10.1: dmap; 1,1'-Thiocarbonyldiimidazole / dichloromethane

10.2: 100 °C

11.1: dowex 50W₈X

12.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile

13.1: potassium carbonate; methanol

14.1: 1,1'-Thiocarbonyldiimidazole

With pyridine; methanol; dmap; N,O-bis-(trimethylsilyl)-acetamide; boron trifluoride diethyl etherate; sulfur trioxide; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; 1,1'-Thiocarbonyldiimidazole; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; sulfuric acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
L-(+)-arabinose

: 1352234-63-9
1-((2R,3aR,7S,7aS)-7-(benzyloxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:: Multi-step reaction with 15 steps

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

2.1: copper(II) sulfate / sulfuric acid

3.1: sodium hydride; tetrabutyl ammonium fluoride / N,N-dimethyl-formamide; tetrahydrofuran

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran

5.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide; pyridine / dichloromethane; dimethyl sulfoxide

6.1: boron trifluoride diethyl etherate / dichloromethane / -78 °C

7.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran

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

9.1: pyridinium chlorochromate

10.1: L-proline

11.1: dmap; 1,1'-Thiocarbonyldiimidazole / dichloromethane

11.2: 100 °C

12.1: dowex 50W₈X

13.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile

14.1: potassium carbonate; methanol

15.1: 1,1'-Thiocarbonyldiimidazole

With pyridine; 1H-imidazole; methanol; dmap; N,O-bis-(trimethylsilyl)-acetamide; boron trifluoride diethyl etherate; sulfur trioxide; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; 1,1'-Thiocarbonyldiimidazole; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; sulfuric acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;