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

Base Information

• Chemical Name: 2,5-anhydro-3-azido-6-O-benzoyl-3-deoxy-4-O-hexanoyl-D-allononitrile
• CAS No.: 888026-86-6
• Molecular Formula: C₁₉H₂₂N₄O₅
• Molecular Weight: 386.407
• Mol file: 888026-86-6.mol

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

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

There total 7 articles about 2,5-anhydro-3-azido-6-O-benzoyl-3-deoxy-4-O-hexanoyl-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: 68.0%

Benzoic acid (2R,3S,4S,5R)-4-azido-3-hexanoyloxy-5-(hydroxyimino-methyl)-tetrahydro-furan-2-ylmethyl ester → 2,5-anhydro-3-azido-6-O-benzoyl-3-deoxy-4-O-hexanoyl-D-allononitrile (888026-86-6)

Guidance literature:

With pyridine; methanesulfonyl chloride; at -15 - 20 ℃; for 2.75h;

DOI:10.1016/j.tet.2011.06.090

Reference yield:

2,5-anhydro-4-O-n-hexanoyl-3,6-di-O-methanesulfonyl-D-glucoseethylene acetal (888026-83-3) → 2,5-anhydro-3-azido-6-O-benzoyl-3-deoxy-4-O-hexanoyl-D-allononitrile (888026-86-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / dimethylformamide / 12 h / 100 °C

2.1: 47 percent / sodium azide / dimethylsulfoxide / 24 h / 110 °C

3.1: trifluoroacetic acid; aq. hydrochloric acid / 120 h / 4 °C

3.2: hydroxylamine hydrochloride; NaOAc / ethanol / 4 h / 20 °C

4.1: mesyl chloride; pyridine / 2 h / -15 - 20 °C

With pyridine; hydrogenchloride; sodium azide; methanesulfonyl chloride; trifluoroacetic acid; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.02.001

Reference yield:

2,5-anhydro-6-O-benzoyl-4-O-hexanoyl-3-O-methanesulfonyl-D-glucose ethylene acetal (888026-84-4) → 2,5-anhydro-3-azido-6-O-benzoyl-3-deoxy-4-O-hexanoyl-D-allononitrile (888026-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 47 percent / sodium azide / dimethylsulfoxide / 24 h / 110 °C

2.1: trifluoroacetic acid; aq. hydrochloric acid / 120 h / 4 °C

2.2: hydroxylamine hydrochloride; NaOAc / ethanol / 4 h / 20 °C

3.1: mesyl chloride; pyridine / 2 h / -15 - 20 °C

With pyridine; hydrogenchloride; sodium azide; methanesulfonyl chloride; trifluoroacetic acid; In dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2006.02.001

upstream raw materials:

2,5-anhydro-4-O-n-hexanoyl-3,6-di-O-methanesulfonyl-D-glucoseethylene acetal

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

2,5-anhydro-6-O-benzoyl-4-O-hexanoyl-3-O-methanesulfonyl-D-glucose ethylene acetal

Potassium benzoate

Downstream raw materials:

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

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