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

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

C₃₂H₂₅N₃O₉

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

Refernces

• 1、 Xiao, Chuan,Sun, Chao,Han, Weiwei,Pan, Feng,Dan, Zhu,Li, Yu,Song, Zhi-Guang,Jin, Ying-Hua. "Synthesis of 6-(het) ary Xylocydine analogues and evaluating their inhibitory activities of CDK1 and CDK2 in vitro". experimental part. p. 7100 - 7110. Retrieved 2012/01/14.
• 2、 Forsman, Jonas J.,Waerna, Johan,Murzin, Dmitry Yu,Leino, Reko. "Reaction kinetics and mechanism of sulfuric acid-catalyzed acetolysis of acylated methyl l-ribofuranosides". experimental part. p. 5666 - 5676. Retrieved 2010/03/03.