2-(1'-Imidazoylsulfonyl)-1,3,5-tri-O-benzoyl-alpha-D-ribofuranose

Base Information

• Chemical Name: 2-(1'-Imidazoylsulfonyl)-1,3,5-tri-O-benzoyl-alpha-D-ribofuranose
• CAS No.: 97614-42-1
• Molecular Formula: C29H24N2O10S
• Molecular Weight: 592.583
• Nikkaji Number: J698.328F
• Mol file: 97614-42-1.mol

Synonyms:97614-42-1;2-(1'-Imidazoylsulfonyl)-1,3,5-tri-O-benzoyl-alpha-D-ribofuranose;1,3,5-Tri-O-benzoyl-2-O-(1'-imidazoylsulfonyl)-a-D-ribofuranose;(2R,3R,4R,5R)-3-(((1H-Imidazol-1-yl)sulfonyl)oxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2,4-diyl dibenzoate;SCHEMBL10599457;[(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-imidazol-1-ylsulfonyloxyoxolan-2-yl]methyl benzoate;BS-33425;W-204162;2-O-[(1H-Imidazol-1-yl)sulfonyl]-1-O,3-O,5-O-tribenzoyl-alpha-D-ribofuranose;(2R,3R,4R,5R)-3-(((1H-Imidazol-1-yl)sulfonyl)oxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2,4-diyldibenzoate;(2R,3R,4R,5R)-3-(1H-imidazol-1-ylsulfonyloxy)-5-(benzoyloxymethyl)tetrahydrofuran-2,4-diyl dibenzoate;(2R,3R,4R,5R)-5-(benzoyloxy)-2-[(benzoyloxy)methyl]-4-[(1H-imidazole-1-sulfonyl)oxy]oxolan-3-yl benzoate

Chemical Property of 2-(1'-Imidazoylsulfonyl)-1,3,5-tri-O-benzoyl-alpha-D-ribofuranose

Chemical Property:

• Boiling Point: 749.9 ºC at 760 mmHg
• Flash Point: 407.3 ºC
• PSA: 157.70000
• Density: 1.42 g/cm³
• LogP: 4.10650
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 13
• Exact Mass: 592.11516614
• Heavy Atom Count: 42
• Complexity: 1030

Purity/Quality:

99% ^*data from raw suppliers

1,3,5-Tri-O-benzoyl-2-O-(1H-imidazol-1-ylsulfonyl)-α-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)OC(=O)C3=CC=CC=C3)OS(=O)(=O)N4C=CN=C4)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@H]([C@H](O2)OC(=O)C3=CC=CC=C3)OS(=O)(=O)N4C=CN=C4)OC(=O)C5=CC=CC=C5
• Uses: 1,3,5-Tri-O-benzoyl-2-O-(1H-imidazol-1-ylsulfonyl)-alpha-D-ribofuranose is used in the preparation of clofarabine (nucleoside analog) for cancer treatment

Technology Process of 2-(1'-Imidazoylsulfonyl)-1,3,5-tri-O-benzoyl-alpha-D-ribofuranose

There total 1 articles about 2-(1'-Imidazoylsulfonyl)-1,3,5-tri-O-benzoyl-alpha-D-ribofuranose 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: 76.0%

1H-imidazole (288-32-4) + 1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-42-1)

Guidance literature:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside; With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at -15 - 20 ℃;

1H-imidazole; In dichloromethane; at 0 - 20 ℃;

Reference yield: 77.0%

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-42-1) → 2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-50-1)

Guidance literature:

With triethylamine hydrofluoride; In ethyl acetate;

Reference yield: 66.4%

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-42-1) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In ethyl acetate; at 60 - 70 ℃; for 4.5h;

upstream raw materials:

1H-imidazole

1,3,5-tri-O-benzoyl-α-D-ribofuranoside

Downstream raw materials:

β-phenyl hydroxypropionate

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

C₂₈H₂₆O₉

2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

Refernces