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

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 oxime
• CAS No.: 374081-60-4
• Molecular Formula: C₃₀H₃₀BrN₃O₅
• Molecular Weight: 592.489
• Mol file: 374081-60-4.mol

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

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

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 oxime

There total 7 articles about 3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbaldehyde oxime 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:

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

Guidance literature:

With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; water; at 20 ℃; for 2h;

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 oxime (374081-60-4)

Guidance literature:

Multi-step reaction with 4 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

With ethylmagnesium bromide; hydroxylamine hydrochloride; ammonia; 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-carbaldehyde oxime (374081-60-4)

Guidance literature:

Multi-step reaction with 5 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

With N,O-bis-(trimethylsilyl)-acetamide; ethylmagnesium bromide; hydroxylamine hydrochloride; ammonia; 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

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

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