3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside

Base Information

• Chemical Name: 3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside
• CAS No.: 1448452-79-6
• Molecular Formula: C₃₃H₃₁N₃O₇
• Molecular Weight: 581.625

Synonyms:3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside

Chemical Property of 3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside

Chemical Property:

Purity/Quality:

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Technology Process of 3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside

There total 6 articles about 3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-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: 87.0%

C19H23N3O5 (1448452-80-9) + benzoyl chloride (98-88-4) → 3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside (1448452-79-6)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c3ob40958a

Reference yield:

phenyl 3,5-O-(di-tert-butylsilanediyl)-2-O-2-naphthylmethyl-1-thio-α-L-arabinofuranoside (1448452-68-3) → 3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside (1448452-79-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 0.25 h / -40 - 20 °C / Molecular sieve; Inert atmosphere

2.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere

3.1: pyridine; pyridine hydrogenfluoride / dichloromethane / 2 h / 0 °C / Inert atmosphere

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

With pyridine; sodium azide; pyridine hydrogenfluoride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c3ob40958a

Reference yield:

2-bromomethylnaphthyl bromide (939-26-4) → 3-azidopropyl 3,5-di-O-benzoyl-2-O-2-naphthylmethyl-β-arabinofuranoside (1448452-79-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere

2.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 0.25 h / -40 - 20 °C / Molecular sieve; Inert atmosphere

3.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere

4.1: pyridine; pyridine hydrogenfluoride / dichloromethane / 2 h / 0 °C / Inert atmosphere

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

With pyridine; sodium azide; sodium hydride; pyridine hydrogenfluoride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c3ob40958a

upstream raw materials:

phenyl 3,5-O-(di-tert-butylsilanediyl)-2-O-2-naphthylmethyl-1-thio-α-L-arabinofuranoside

C₁₉H₂₃N₃O₅

benzoyl chloride

phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-L-arabinofuranoside

Downstream raw materials:

3-azidopropyl 3,5-di-O-benzoyl-β-L-arabinofuranoside

3-azidopropyl 3,5-O-(di-tert-butylsilanediyl)-2-O-2-naphthylmethyl-β-L-arabinofuranosyl-(1→2)-3,5-di-O-benzoyl-β-L-arabinofuranoside

C₄₆H₅₅N₃O₁₁Si

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