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

Base Information

• Chemical Name: methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate
• CAS No.: 874460-60-3
• Molecular Formula: C₁₇H₁₉N₃O₇
• Molecular Weight: 377.354
• Mol file: 874460-60-3.mol

Synonyms:methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate

Chemical Property of methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate

There total 3 articles about methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate 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: 0.17%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (3aR,6S,7S,7aR)-6-Azido-7-benzoyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid → methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate (874460-60-3)

Guidance literature:

In methanol; diethyl ether; at 0 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(01)01845-7

Reference yield:

2-azido-3-O-benzyl-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose (402589-09-7) → methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate (874460-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ruthenium(III) chloride hydrate; sodium metaperiodate / acetonitrile; H₂O; CCl₄ / 0.25 h / 20 °C

2: 0.17 percent / methanol; diethyl ether / 0.33 h / 0 °C

With ruthenium trichloride; sodium periodate; In methanol; tetrachloromethane; diethyl ether; water; acetonitrile;

DOI:10.1016/j.tet.2005.09.128

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) → methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate (874460-60-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: ruthenium(III) chloride hydrate; sodium metaperiodate / acetonitrile; H₂O; CCl₄ / 0.25 h / 20 °C

3: 0.17 percent / methanol; diethyl ether / 0.33 h / 0 °C

With ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; water; acetonitrile;

DOI:10.1016/j.tet.2005.09.128

upstream raw materials:

diazomethane

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

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

Downstream raw materials:

methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate