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

Base Information

• Chemical Name: 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal
• CAS No.: 228399-09-5
• Molecular Formula: C₂₂H₂₃N₃O₆
• Molecular Weight: 425.441
• Mol file: 228399-09-5.mol

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

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

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-allose ethylene acetal

There total 5 articles about 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal 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: 77.0%

2,5-anhydro-6-O-benzoyl-4-O-benzyl-3-O-methanesulfonyl-D-glucose ethylene acetal (228398-95-6) → 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal (228399-09-5)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 120 ℃; for 47h;

DOI:10.1016/S0040-4039(00)00894-7

Reference yield: 77.0%

2,5-anhydro-6-O-benzoyl-4-O-benzyl-3-O-methanesulfonyl-D-glucose ethylene acetal (228398-95-6) → 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal (228399-09-5) + Benzoic acid (2R,3S)-3-benzyloxy-5-[1,3]dioxolan-2-yl-2,3-dihydro-furan-2-ylmethyl ester

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 115 - 120 ℃; for 47h;

DOI:10.1016/S0040-4020(01)01126-7

Reference yield:

Potassium benzoate (582-25-2) → 2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal (228399-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / dimethylformamide / 48 h / 100 °C

2: 77 percent / NaN₃ / dimethylsulfoxide / 47 h / 115 - 120 °C

With sodium azide; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01126-7

upstream raw materials:

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

Potassium benzoate

2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal

2,5-anhydro-4-O-benzyl-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal

Downstream raw materials:

2,5-anhydro-3-benzamido-4,6-di-O-benzoyl-3-deoxy-D-allose ethylene acetal

methyl Z-4,7-anhydro-5-benzamido-6,8-di-O-benzoyl-2,3,5-trideoxy-D-allo-oct-2-enoate

methyl E-4,7-anhydro-5-benzamido-6,8-di-O-benzoyl-2,3,5-trideoxy-D-allo-oct-2-enoate

4-((2S,3S,4S,5R)-3-Benzoylamino-4-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrazole-3-carboxylic acid methyl ester