methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate

Base Information

• Chemical Name: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate
• CAS No.: 132591-29-8
• Molecular Formula: C₂₃H₃₃NO₁₃
• Molecular Weight: 531.514
• Mol file: 132591-29-8.mol

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate

Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate

There total 1 articles about methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate 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: 79.0%

C20H28BrNO13 + allyltributylstanane (24850-33-7) → methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate (132591-29-8) + methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl)onate (20298-34-4,84380-10-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; at 20 - 80 ℃; for 8.33333h; under 100 Torr; Solvent; Temperature; Time; Concentration; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.12.064

Reference yield: 85.0%

1-ethenyl-4-methylbenzene (622-97-9,24936-41-2) + methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate (132591-29-8) → methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-β-D-erythro-L-gluco-non-2-ulopyranosonate

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 - 40 ℃; for 48h;

DOI:10.1016/j.tetlet.2012.12.064

Reference yield:

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate (132591-29-8) → methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(p-tolyl)-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine; dmap / 16 h / 20 °C / Inert atmosphere

2.1: acetyl chloride / methanol; dichloromethane / 48 h / 0 - 20 °C / Cooling with ice

2.2: 16 h / 0 - 20 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 40 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; acetyl chloride; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2012.12.064

upstream raw materials:

allyltributylstanane