octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside

Base Information

• Chemical Name: octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside
• CAS No.: 685111-74-4
• Molecular Formula: C₄₆H₄₉FO₁₂
• Molecular Weight: 812.886
• Mol file: 685111-74-4.mol

Synonyms:octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property of octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside

There total 5 articles about octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-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: 92.0%

octyl 2,5-di-O-benzoyl-α-D-arabinofuranoside (569659-32-1) + p-toluyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-1-thio-α-D-arabinofuranoside (685111-63-1) → octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside (685111-74-4)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1016/j.carres.2003.12.015

Reference yield:

p-methylphenyl 1-thio-α-D-arabinofuranoside (204918-49-0) → octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside (685111-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1: DMAP / pyridine; CH₂Cl₂ / 20 °C

2: 85 percent / pyridine / 20 °C

3: 86 percent / p-toluenesulfonic acid / methanol; CH₂Cl₂ / 20 °C

4: 60 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / -40 - 20 °C

5: 92 percent / N-iodosuccinimide; silver triflate / CH₂Cl₂ / 0.08 h / 0 °C

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

DOI:10.1016/j.carres.2003.12.015

Reference yield:

p-toluyl 2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside (685111-68-6) → octyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-α-D-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-D-arabinofuranoside (685111-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / -40 - 20 °C

2: 92 percent / N-iodosuccinimide; silver triflate / CH₂Cl₂ / 0.08 h / 0 °C

With N-iodo-succinimide; diethylamino-sulfur trifluoride; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/j.carres.2003.12.015

upstream raw materials:

octyl 2,5-di-O-benzoyl-α-D-arabinofuranoside

p-toluyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-1-thio-α-D-arabinofuranoside

p-methylphenyl 1-thio-α-D-arabinofuranoside

p-toluyl 2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside