1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

Base Information

• Chemical Name: 1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose
• CAS No.: 14215-97-5
• Molecular Formula: C28H24 O9
• Molecular Weight: 504.493
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID20448642
• Nikkaji Number: J285.076A
• Mol file: 14215-97-5.mol

Synonyms:1-A-TB-R cpd;1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose;1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranose

Chemical Property of 1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

Chemical Property:

• Melting Point: 126-127 °C
• Refractive Index: 1.61
• Boiling Point: 621.0±55.0 °C(Predicted)
• PSA: 114.43000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 3.58260
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 504.14203234
• Heavy Atom Count: 37
• Complexity: 794

Purity/Quality:

98%, ^*data from raw suppliers

1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(C(O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: CC(=O)OC1[C@@H]([C@@H]([C@H](O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Uses: An inhibitor of neutrophil-keyhole limpet hemocyanin adhesion

Technology Process of 1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

There total 46 articles about 1-O-Acetyl-2,3,5-tri-O-benzoyl-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: 54.0%

acetic anhydride (108-24-7) + Methyl 2,3,5-tri-O-benzoyl-L-ribofuranoside → 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6,6974-32-9,14215-97-5,16162-35-9,20822-87-1,21138-42-1,22249-15-6,22249-17-8,26287-72-9,53403-35-3,53403-36-4,57236-69-8,70832-64-3,99395-04-7,100101-51-7,109668-83-9,120019-54-7) + 1,4-di-O-acetyl-2,3,5-tri-O-benzoyl-L-ribose methyl hemiacetal + 1,1,4-tri-O-acetyl-2,3,5-tri-O-benzoyl-L-ribose

Guidance literature:

With sulfuric acid; In acetic acid; at -35 - -10 ℃; for 0.25h;

Reference yield: 48.0%

L-ribose (24259-59-4) + acetic anhydride (108-24-7) + benzoyl chloride (98-88-4) → 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6,6974-32-9,14215-97-5,16162-35-9,20822-87-1,21138-42-1,22249-15-6,22249-17-8,26287-72-9,53403-35-3,53403-36-4,57236-69-8,70832-64-3,99395-04-7,100101-51-7,109668-83-9,120019-54-7)

Guidance literature:

L-ribose; With hydrogenchloride; In methanol; at 20 ℃; for 6h;

benzoyl chloride; With pyridine; In dichloromethane; at 20 ℃;

acetic anhydride; With sulfuric acid; In acetic acid; at 20 ℃;

Reference yield: 45.0%

acetic anhydride (108-24-7) + methyl 2,3,5-tri-O-benzoyl-αβ-D-ribofuranoside (69350-76-1) → 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6,6974-32-9,14215-97-5,16162-35-9,20822-87-1,21138-42-1,22249-15-6,22249-17-8,26287-72-9,53403-35-3,53403-36-4,57236-69-8,70832-64-3,99395-04-7,100101-51-7,109668-83-9,120019-54-7)

Guidance literature:

With sulfuric acid; acetic acid; at 0 ℃;

upstream raw materials:

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

methyldopa

carboxymethyl-1 N-acetyl-2 (dihydroxy-3,4 phenyl)-3 alanine

carboxymethyl-1 methyl-2 N-acetyl-2 (dihydroxy-3,4 phenyl)-3 alanine

Downstream raw materials:

4,6-dimethylthio-1-(2',3',5'-tri-O-benzoyl-α-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidine

4,6-dimethylthio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidine

4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrazolo<4,3-d>pyrimidine-5,7-(1H,6H)-dione

ethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)indolin-3-acetate

Refernces

Efficient synthesis of clitocine via 1,3-N (endo) to N (exo) migration: A revision to Kini's work

10.1055/s-2005-871564

The research aims to develop an efficient synthesis method for clitocine, a compound with significant biological activity, including insecticidal properties and cytostatic effects on leukemia cell lines. The study revisits Kini's previous work and introduces a novel synthetic pathway involving a 1,3-N (endo) to N (exo) migration as a key transformation. The researchers used p-chlorobenzoyl (PCB) as a protecting group to facilitate the solidification of intermediates and minimize epimerization at the final deprotection stage. Key chemicals used in the synthesis include 4,6-diamino-5-nitropyrimidine, 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose, and silica gel for isomerization. The study concludes that the endo-product formed during glycosylation is kinetically favored but isomerizes to the thermodynamically stable exo-product under acid catalysis. The incorporation of the PCB group significantly improves the isolation and purification of intermediates. The final deprotection step using methanol and sodium methoxide yields highly pure clitocine without any column separation, demonstrating a more efficient and practical synthesis route compared to previous methods.