n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Base Information

• Chemical Name: n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside
• CAS No.: 527681-80-7
• Molecular Formula: C₃₉H₄₄O₁₁
• Molecular Weight: 688.772
• Mol file: 527681-80-7.mol

Synonyms:n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property of n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

There total 5 articles about n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside 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: 84.0%

octyl 2,3-di-O-benzoyl-α-D-arabinofuranoside (329360-19-2) + p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-β-D-ribofuranoside (527680-93-9) → n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside (527681-80-7)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 0.166667h;

DOI:10.1016/j.tet.2003.12.022

Reference yield:

octyl 2,3-di-O-benzoyl-α-D-arabinofuranoside (329360-19-2) + p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-β-D-ribofuranoside (527680-93-9) → C39H44O11 + n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside (527681-80-7)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -40 ℃;

DOI:10.1021/ja029302m

Reference yield:

benzoyl chloride (98-88-4) → n-octyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside (527681-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine; DMAP / CH₂Cl₂ / 20 °C

1.2: 97 percent / CH₂Cl₂ / 20 °C

2.1: 94 percent / p-TsOH / CH₂Cl₂; methanol / 12 h / 20 °C

3.1: 84 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0.17 h / -40 °C

With pyridine; dmap; N-iodo-succinimide; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.12.022

upstream raw materials:

octyl 2,3-di-O-benzoyl-α-D-arabinofuranoside

p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-β-D-ribofuranoside

benzoyl chloride