benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate
• CAS No.: 121409-22-1
• Molecular Formula: C₂₆H₃₀O₁₃
• Molecular Weight: 550.516
• Mol file: 121409-22-1.mol

Synonyms:benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate

Chemical Property of benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate

There total 9 articles about benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate 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: 97.0%

benzyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl chlorid)onate (123269-89-6) → benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate (121409-22-1)

Guidance literature:

With triethylamine; 2-hydroxynitrobenzene; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1055/s-1998-1717

Reference yield: 18.3%

2',3'-O-isopropylideneuridine (362-43-6) + benzyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl bromide)onate (121409-13-0) → benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate (121409-22-1) + O-[benzyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-β-D-glycero-D-galactononulopyranosyl)onate]-(2-5')-2',3'-O-isopropylideneuridine + O-[benzyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-α-D-glycero-D-galactononulopyranosyl)onate]-(2-5')-2',3'-O-isopropylideneuridine + O-[benzyl (4,6,7,8,9-penta-O-acetyl-3-deoxy-β-D-glycero-D-galactononulofuranosyl)onate]-(2-5')-2',3'-O-isopropylideneuridine + O-[benzyl (4,6,7,8,9-penta-O-acetyl-3-deoxy-α-D-glycero-D-galactononulofuranosyl)onate]-(2-5')-2',3'-O-isopropylideneuridine

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In dichloromethane; for 72h; Mechanism; Ambient temperature; other uridine derivatives; other reagents;

DOI:10.1248/cpb.45.795

Reference yield: 16.0%

benzyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl chlorid)onate (123269-89-6) + 2-hydroxynitrobenzene (88-75-5,78813-12-4) → benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate (121409-22-1) + (2S,4S,5R,6R)-4,5-Diacetoxy-2-(2-nitro-phenoxy)-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1055/s-1998-1717

upstream raw materials:

cholesterol

benzyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl bromide)onate

2',3'-O-isopropylideneuridine

4-nitro-phenol