1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one

Base Information

• Chemical Name: 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one
• CAS No.: 1345024-34-1
• Molecular Formula: C₂₈H₃₁N₅O₃Si
• Molecular Weight: 513.671

Synonyms:1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one

Chemical Property of 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one

There total 13 articles about 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one 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: 95.0%

1,2,4-Triazole (288-88-0) + 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidine-2,4(1H,3H)-dione (1345024-27-2) → 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (1345024-34-1)

Guidance literature:

1,2,4-Triazole; With triethylamine; trichlorophosphate; In acetonitrile; at 0 ℃; for 1h; Inert atmosphere;

1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidine-2,4(1H,3H)-dione; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo201716c

Reference yield:

tert-Butyl-[(R)-1-(2,3-dihydro-furan-3-yl)methoxy]-diphenyl-silane (287933-72-6) → 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (1345024-34-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1.25 h / -78 - 0 °C / Inert atmosphere

1.2: 1.25 h / -78 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diethylzinc / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 20 °C / Inert atmosphere

5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; acetone / 1 h / 0 - 20 °C / Inert atmosphere

5.2: 20 °C / pH 2 - 3 / Inert atmosphere

6.1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 0 - 20 °C / Inert atmosphere

7.1: toluene / 2 h / 80 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 °C / Inert atmosphere

9.1: ammonium hydroxide / ethanol; water / 5 h / 100 °C / Inert atmosphere; Sealed tube

10.1: triethylamine; trichlorophosphate / acetonitrile / 1 h / 0 °C / Inert atmosphere

10.2: 0 - 20 °C / Inert atmosphere

With ammonium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; diphenyl phosphoryl azide; tert.-butyl lithium; diethylzinc; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; pentane; 3.1: Simmons-Smith reaction / 4.1: Swern oxidation / 4.2: Swern oxidation / 7.1: Curtius rearrangement;

DOI:10.1021/jo201716c

Reference yield:

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate (1345023-89-3) → 1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (1345024-34-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 96 h / Inert atmosphere

2.1: sodium hydride / mineral oil / 0 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: diethylzinc / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

5.1: sodium periodate; ruthenium trichloride; sodium hydrogencarbonate / chloroform; water; acetonitrile / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 0 - 20 °C / Inert atmosphere

7.1: toluene / 2 h / 80 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 °C / Inert atmosphere

9.1: ammonium hydroxide / ethanol; water / 5 h / 100 °C / Inert atmosphere; Sealed tube

10.1: triethylamine; trichlorophosphate / acetonitrile / 1 h / 0 °C / Inert atmosphere

10.2: 0 - 20 °C / Inert atmosphere

With ruthenium trichloride; ammonium hydroxide; sodium periodate; n-butyllithium; diphenyl phosphoryl azide; diethylzinc; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; water; toluene; acetonitrile; mineral oil; 4.1: Simmons-Smith reaction / 7.1: Curtius rearrangement;

DOI:10.1021/jo201716c

upstream raw materials:

1,2,4-Triazole

1-((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidine-2,4(1H,3H)-dione

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxytetrahydrofuran-2-carbonitrile

Downstream raw materials:

C₂₆H₃₁N₃O₃Si

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