2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose

Base Information

• Chemical Name: 2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose
• CAS No.: 874460-57-8
• Molecular Formula: C₁₆H₁₉N₃O₅
• Molecular Weight: 333.344
• Mol file: 874460-57-8.mol

Synonyms:

Chemical Property of 2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose

There total 1 articles about 2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-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:

((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane (364635-35-8) → 2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose (874460-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / tetrabutyl ammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

2: 92 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 0.08 h / -70 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;

DOI:10.1016/j.tet.2005.09.128

Reference yield:

2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose (874460-57-8) → (3aR,6S,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 0 ℃;

DOI:10.1016/j.tet.2005.09.128

Reference yield:

2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose (874460-57-8) → methyl (3-O-benzyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ulopyranosyl amine)onate

Guidance literature:

Multi-step reaction with 3 steps

1: NaClO₂; NaH₂PO₄*2H₂O; 2-methylbut-2-ene / 2-methyl-propan-2-ol; H₂O / 0 °C

2: 0.089 g / diethyl ether; methanol / 0.33 h / 0 °C

3: hydrogen / palladium on carbon / methanol / 1 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; palladium on activated charcoal; In methanol; diethyl ether; water; tert-butyl alcohol;

DOI:10.1016/j.tet.2005.09.128

upstream raw materials:

((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane

Downstream raw materials:

methyl (3-O-benzyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ulopyranosyl azide)onate