1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose

Base Information

• Chemical Name: 1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• CAS No.: 128333-75-5
• Molecular Formula: C₁₉H₂₄N₄O₇
• Molecular Weight: 420.422
• Mol file: 128333-75-5.mol

Synonyms:1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose

Chemical Property of 1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose

There total 2 articles about 1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 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%

((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanamine (128316-82-5) + succinimide 4-azidosalicylate (96602-46-9) → 1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose (128333-75-5)

Guidance literature:

In N,N-dimethyl-formamide; at 25 ℃; for 48h;

DOI:10.1016/0008-6215(89)85100-6

Reference yield:

(3aS,5aR,8aR,8bS)-3a-(azidomethyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran (78574-36-4) → 1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose (128333-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / hydrogen / 5 percent palladium on carbon / ethanol / 25 °C / 2585.7 Torr

2: 87 percent / dimethylformamide / 48 h / 25 °C

With hydrogen; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)85100-6

Reference yield: 41.0%

1-(4-azido-2-hydroxybenzamido)-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose (128333-75-5) → 1-(4-azido-2-hydroxybenzamido)-1-deoxy-β-D-fructose

Guidance literature:

With acidic cation-exchange resin; In methanol; water; at 48 - 50 ℃; for 5h;

DOI:10.1016/0008-6215(89)85100-6

upstream raw materials:

((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanamine

succinimide 4-azidosalicylate

(3aS,5aR,8aR,8bS)-3a-(azidomethyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran