1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 1352744-33-2
• Molecular Formula: C₄₁H₄₁N₅O₁₁
• Molecular Weight: 779.803

Synonyms:1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property of 1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

There total 6 articles about 1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-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: 57.0%

5-methyl-3-(pivaloyloxymethyl)-1-[(1H-1,2,3-triazol-4-yl)methyl]pyrimidine-2,4(1H,3H)-dione + (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate (1352744-35-4) → 1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione (1352744-33-2) + 1-((2-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione (1352744-32-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 - 22 ℃; for 24h;

DOI:10.1016/j.tet.2011.10.067

Reference yield:

3-(pivaloyloxymethyl)-1-propargylthymine (1352744-23-0) → 1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione (1352744-33-2) + 1-((2-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione (1352744-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilylazide / toluene / 24 h / 120 °C / Inert atmosphere

1.2: 1 h / 20 - 22 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 24 h / 20 - 22 °C

With trimethylsilylazide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2011.10.067

Reference yield:

Chloromethyl pivalate (18997-19-8) → 1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione (1352744-33-2) + 1-((2-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione (1352744-32-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 - 22 °C

1.2: 48 h / 20 - 22 °C

2.1: trimethylsilylazide / toluene / 24 h / 120 °C / Inert atmosphere

2.2: 1 h / 20 - 22 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 24 h / 20 - 22 °C

With trimethylsilylazide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2011.10.067

upstream raw materials:

((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate

benzoyl chloride

(2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate

3-(pivaloyloxymethyl)-1-propargylthymine

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