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

Base Information

• Chemical Name: 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde
• CAS No.: 374081-59-1
• Molecular Formula: C₃₀H₂₉BrN₂O₅
• Molecular Weight: 577.475
• Mol file: 374081-59-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde 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:

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,5-dibromo-1H-imidazole (374081-58-0) → 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde (374081-59-1)

Guidance literature:

With ethylmagnesium bromide; In diethyl ether; at 20 ℃; for 23h;

DOI:10.1021/jo0255476

Reference yield:

1,2,3,5-tetraacetylribose (13035-61-5) → 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde (374081-59-1)

Guidance literature:

Multi-step reaction with 4 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

4.1: ethylmagnesium bromide / diethyl ether / 23 h / 20 °C

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

DOI:10.1021/jo0255476

Reference yield:

4,5-dibromo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole (437614-21-6) → 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde (374081-59-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: ethylmagnesium bromide / diethyl ether / 23 h / 20 °C

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

DOI:10.1021/jo0255476

upstream raw materials:

N,N-dimethyl-formamide

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

benzyl bromide

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

Downstream raw materials:

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

2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide