2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile

Base Information

• Chemical Name: 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile
• CAS No.: 781642-71-5
• Molecular Formula: C₂₀H₁₈N₄O₄
• Molecular Weight: 378.387
• Mol file: 781642-71-5.mol

Synonyms:2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile

Chemical Property of 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile

There total 3 articles about 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile 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:

Benzoic acid (2R,3S,4S,5R)-4-azido-3-benzyloxy-5-(hydroxyimino-methyl)-tetrahydro-furan-2-ylmethyl ester → 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile (781642-71-5)

Guidance literature:

With pyridine; methanesulfonyl chloride; at -15 - 20 ℃; for 2.5h;

DOI:10.1016/j.tetlet.2004.07.104

Reference yield:

2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal (228399-09-5) → 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile (781642-71-5)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA; aq. HCl / 72 h / 4 °C

2: NH₂OH*HCl; NaOAc / ethanol; CH₂Cl₂ / 2 h / 20 °C

3: MsCl; pyridine / 2.5 h / -15 - 20 °C

With pyridine; hydrogenchloride; hydroxylamine hydrochloride; sodium acetate; methanesulfonyl chloride; trifluoroacetic acid; In ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2004.07.104

Reference yield:

Benzoic acid (2R,3S,4R,5R)-4-azido-3-benzyloxy-5-formyl-tetrahydro-furan-2-ylmethyl ester → 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allononitrile (781642-71-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₂OH*HCl; NaOAc / ethanol; CH₂Cl₂ / 2 h / 20 °C

2: MsCl; pyridine / 2.5 h / -15 - 20 °C

With pyridine; hydroxylamine hydrochloride; sodium acetate; methanesulfonyl chloride; In ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2004.07.104

upstream raw materials:

2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal

Downstream raw materials:

2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allonothioamide

ethyl 2-(2-azido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate

2,5-anhydro-3-azido-6-O-benzoyl-3-deoxy-D-allonothioamide

2-(4-carboethoxythiazol-2-yl)-5-((benzoyloxy)methyl)furan