allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside

Base Information

• Chemical Name: allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside
• CAS No.: 1431388-92-9
• Molecular Formula: C₂₂H₂₃N₃O₇S
• Molecular Weight: 473.507
• Mol file: 1431388-92-9.mol

Synonyms:allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside

Chemical Property of allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside

There total 4 articles about allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-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: 79.0%

allyl 3-azido-5-O-benzoyl-3-deoxy-α-D-arabinofuranoside (1431388-91-8) + p-toluenesulfonyl chloride (98-59-9) → allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside (1431388-92-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 50h; Inert atmosphere;

DOI:10.1016/j.tet.2013.03.074

Reference yield:

allyl α-D-arabinofuranoside (103702-75-6,773896-71-2) → allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside (1431388-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2.17 h / 0 - 20 °C / Inert atmosphere

2: sodium azide; ammonium chloride / ethanol; water / 48 h / Inert atmosphere; Reflux

3: pyridine / dichloromethane / 50 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium azide; di-isopropyl azodicarboxylate; ammonium chloride; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1016/j.tet.2013.03.074

Reference yield:

allyl 2,3-anhydro-5-O-benzoyl-α-D-lyxofuranoside (1431388-88-3) → allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside (1431388-92-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide; ammonium chloride / ethanol; water / 48 h / Inert atmosphere; Reflux

2: pyridine / dichloromethane / 50 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium azide; ammonium chloride; In ethanol; dichloromethane; water;

DOI:10.1016/j.tet.2013.03.074

upstream raw materials:

allyl 2,3-anhydro-5-O-benzoyl-α-D-lyxofuranoside

allyl 3-azido-5-O-benzoyl-3-deoxy-α-D-arabinofuranoside

p-toluenesulfonyl chloride

allyl α-D-arabinofuranoside

Downstream raw materials:

allyl N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-α-D-ribofuranoside

N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose

N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose