1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole

Base Information

• Chemical Name: 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole
• CAS No.: 374081-58-0
• Molecular Formula: C₂₉H₂₈Br₂N₂O₄
• Molecular Weight: 628.36
• Mol file: 374081-58-0.mol

Synonyms:1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole

Chemical Property of 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole

There total 3 articles about 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole 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: 87.0%

benzyl bromide (100-39-0) + 4,5-dibromo-1-(β-D-ribofuranosyl)imidazole (437614-22-7) → 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole (374081-58-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 6h;

DOI:10.1021/jo0255476

Reference yield:

4,5-dibromo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole (437614-21-6) → 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole (374081-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NH₃ / methanol / 3 h / 100 °C

2: 87 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 0 - 20 °C

With ammonia; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jo0255476

Reference yield:

1,2,3,5-tetraacetylribose (13035-61-5) → 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole (374081-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 5 h / 20 °C

1.2: 66 percent / trimethylsilyltriflate / acetonitrile / 8 h / 0 - 60 °C

2.1: 100 percent / NH₃ / methanol / 3 h / 100 °C

3.1: 87 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 0 - 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; ammonia; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jo0255476

upstream raw materials:

benzyl bromide

4,5-dibromo-1-(β-D-ribofuranosyl)imidazole

4,5-dibromo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole

1,2,3,5-tetraacetylribose

Downstream raw materials:

3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde

3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde oxime

3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbonitrile

6-[3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3H-imidazol-4-yl]-pyrimidin-4-ylamine