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

Base Information

• Chemical Name: 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbonitrile
• CAS No.: 374081-61-5
• Molecular Formula: C₃₀H₂₈BrN₃O₄
• Molecular Weight: 574.474
• Mol file: 374081-61-5.mol

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

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

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-carbonitrile

There total 8 articles about 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbonitrile 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: 90.0%

3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde oxime (374081-60-4) → 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbonitrile (374081-61-5)

Guidance literature:

With acetic anhydride; for 3h; Heating;

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-carbonitrile (374081-61-5)

Guidance literature:

Multi-step reaction with 5 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

4: hydroxylamine hydrochloride; NaHCO₃ / ethanol; H₂O / 2 h / 20 °C

5: 90 percent / acetic anhydride / 3 h / Heating

With ethylmagnesium bromide; hydroxylamine hydrochloride; ammonia; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; water;

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-carbonitrile (374081-61-5)

Guidance literature:

Multi-step reaction with 6 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

5.1: hydroxylamine hydrochloride; NaHCO₃ / ethanol; H₂O / 2 h / 20 °C

6.1: 90 percent / acetic anhydride / 3 h / Heating

With N,O-bis-(trimethylsilyl)-acetamide; ethylmagnesium bromide; hydroxylamine hydrochloride; ammonia; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetonitrile;

DOI:10.1021/jo0255476

upstream raw materials:

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

benzyl bromide

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

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

Downstream raw materials:

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

2-amino-6-[3-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3H-imidazol-4-yl]-3H-pyrimidin-4-one

3-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3H-8-thia-1,3,4,6-tetraaza-cyclopenta[a]inden-7-ylamine

6-amino-1-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-thieno[2,3-d]imidazole-5-carboxylic acid amide