alpha-L-Ribofuranose 1,3,5-tribenzoate 2-(1H-imidazole-1-sulfonate)

Base Information

• Chemical Name: alpha-L-Ribofuranose 1,3,5-tribenzoate 2-(1H-imidazole-1-sulfonate)
• CAS No.: 171720-99-3
• Molecular Formula: C29H24N2O10S
• Molecular Weight: 592.583
• Mol file: 171720-99-3.mol

Synonyms:alpha-L-Ribofuranose 1,3,5-tribenzoate 2-(1H-imidazole-1-sulfonate)

Chemical Property of alpha-L-Ribofuranose 1,3,5-tribenzoate 2-(1H-imidazole-1-sulfonate)

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of alpha-L-Ribofuranose 1,3,5-tribenzoate 2-(1H-imidazole-1-sulfonate)

There total 18 articles about alpha-L-Ribofuranose 1,3,5-tribenzoate 2-(1H-imidazole-1-sulfonate) 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:

benzoyl chloride (98-88-4) → 1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose (171720-99-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / pyridine / 3 h / Ambient temperature

2: 1percent HCl / methanol / 30 h / Ambient temperature

3: pyridine / 3 h / Ambient temperature

4: AcOH, conc. H₂SO₄ / Ambient temperature

5: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

6: 1.) SO₂Cl₂ / 1.) CH₂Cl₂, DMF, from -40 deg C to RT, 3.5 h, 2.) CH₂Cl₂, DMF, RT, 15 h

With pyridine; hydrogenchloride; sulfuryl dichloride; sulfuric acid; water; acetic acid; acetyl chloride; In methanol;

DOI:10.1021/jm960098l

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose (166411-40-1) → 1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose (171720-99-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 79 percent / NaBH₄, H₂O / ethanol / 4 h / Ambient temperature

2: 98 percent / pyridine / 3 h / Ambient temperature

3: 1percent HCl / methanol / 30 h / Ambient temperature

4: pyridine / 3 h / Ambient temperature

5: AcOH, conc. H₂SO₄ / Ambient temperature

6: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

7: 1.) SO₂Cl₂ / 1.) CH₂Cl₂, DMF, from -40 deg C to RT, 3.5 h, 2.) CH₂Cl₂, DMF, RT, 15 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; sulfuryl dichloride; sulfuric acid; water; acetic acid; acetyl chloride; In methanol; ethanol;

DOI:10.1021/jm960098l

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-7α-L-xylofuranose (166411-39-8) → 1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose (171720-99-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 1.5 h / Heating

2: 79 percent / NaBH₄, H₂O / ethanol / 4 h / Ambient temperature

3: 98 percent / pyridine / 3 h / Ambient temperature

4: 1percent HCl / methanol / 30 h / Ambient temperature

5: pyridine / 3 h / Ambient temperature

6: AcOH, conc. H₂SO₄ / Ambient temperature

7: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

8: 1.) SO₂Cl₂ / 1.) CH₂Cl₂, DMF, from -40 deg C to RT, 3.5 h, 2.) CH₂Cl₂, DMF, RT, 15 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; dipyridinium dichromate; sulfuryl dichloride; sulfuric acid; water; acetic anhydride; acetic acid; acetyl chloride; In methanol; ethanol; dichloromethane;

DOI:10.1021/jm960098l

upstream raw materials:

1H-imidazole

1,3,5-Tri-O-benzoyl-α-L-ribofuranose

1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

Downstream raw materials:

1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide

3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl azide

ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl)-1,2,3-triazole-5-carboxylate