1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-arabinofuranose

Base Information

• Chemical Name: 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-arabinofuranose
• CAS No.: 189074-35-9
• Molecular Formula: C₂₈H₂₄O₉
• Molecular Weight: 504.493
• DSSTox Substance ID: DTXSID70466391
• Wikidata: Q82292946

Synonyms:1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-arabinofuranose;SCHEMBL10338159;DTXSID70466391;189074-35-9

Chemical Property of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-arabinofuranose

Chemical Property:

• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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)O[C@H]1[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

Technology Process of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-arabinofuranose

There total 10 articles about 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-arabinofuranose 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: 100.0%

methyl 2,3,5-tri-O-benzoyl-1-α-L-arabinofuranoside (404574-12-5) + acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) → 1-O-Acetyl-2,3,5-tri-O-benzoyl-α/β-L-arabinofuranoside (189074-35-9)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 12h;

Reference yield: 95.0%

acetic anhydride (108-24-7) + 2,3,5-tri-O-benzoyl-1-O-methyl-α-L-arabinofuranose (42793-97-5) → 1-O-Acetyl-2,3,5-tri-O-benzoyl-α/β-L-arabinofuranoside (189074-35-9)

Guidance literature:

With sulfuric acid; In acetic acid; for 4h; Ambient temperature;

DOI:10.1055/s-1991-26543

Reference yield: 80.4%

methyl 2,3,5-tri-O-benzoyl-1-α-L-arabinofuranoside (404574-12-5) + acetic anhydride (108-24-7) → 1-O-Acetyl-2,3,5-tri-O-benzoyl-α/β-L-arabinofuranoside (189074-35-9)

Guidance literature:

With sulfuric acid; In ethyl acetate; at 20 ℃; for 3h;

upstream raw materials:

acetic anhydride

2,3,5-tri-O-benzoyl-1-O-methyl-α-L-arabinofuranose

methyl 2,3,5-tri-O-benzoyl-1-α-L-arabinofuranoside

L-arabinose

Downstream raw materials:

1-<2',3',5'-Tri-O-benzoyl-α-L-arabinofuranosyl>thymine

p-nitrophenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside

N⁴-benzoyl-1-[2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-ribofuranosyl]cytosine

N⁴-benzoyl-1-[5-O-(dimethoxytrityl)-2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-ribofuranosyl]cytosine

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