5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid

Base Information

• Chemical Name: 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid
• CAS No.: 1449035-83-9
• Molecular Formula: C₂₁H₂₈N₂O₇
• Molecular Weight: 420.463

Synonyms:5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid

Chemical Property of 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid

There total 12 articles about 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid 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: 68.0%

methyl 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonate (1449035-99-7) → 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid (1449035-83-9) + 4-acetamido-2,6-anhydro-5-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid

Guidance literature:

With sodium hydroxide; In methanol; water; at 5 - 20 ℃; for 16h; pH=13;

DOI:10.1016/j.bmc.2013.05.054

Reference yield:

1-ethenyl-4-methylbenzene (622-97-9,24936-41-2) → 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid (1449035-83-9) + 4-acetamido-2,6-anhydro-5-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid

Guidance literature:

Multi-step reaction with 9 steps

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

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

3: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 2 h / 60 °C / Inert atmosphere

4: trifluoroacetic acid; water / ethyl acetate / 16 h / 20 °C

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

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide / water; tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

7: sodium methylate / methanol / 2 h / 5 - 20 °C / Inert atmosphere

8: hydrogen sulfide / pyridine / 16 h / 20 °C

9: sodium hydroxide / methanol; water / 16 h / 5 - 20 °C / pH 13

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; trimethylsilyl trifluoromethanesulfonate; hydrogen sulfide; water; sodium methylate; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate;

DOI:10.1016/j.bmc.2013.05.054

Reference yield:

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 → 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid (1449035-83-9) + 4-acetamido-2,6-anhydro-5-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonic acid

Guidance literature:

Multi-step reaction with 8 steps

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

2: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 2 h / 60 °C / Inert atmosphere

3: trifluoroacetic acid; water / ethyl acetate / 16 h / 20 °C

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

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide / water; tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

6: sodium methylate / methanol / 2 h / 5 - 20 °C / Inert atmosphere

7: hydrogen sulfide / pyridine / 16 h / 20 °C

8: sodium hydroxide / methanol; water / 16 h / 5 - 20 °C / pH 13

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; trimethylsilyl trifluoromethanesulfonate; hydrogen sulfide; water; sodium methylate; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; pyridine; methanol; water; ethyl acetate;

DOI:10.1016/j.bmc.2013.05.054

upstream raw materials:

1-ethenyl-4-methylbenzene

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-β-D-erythro-L-gluco-non-2-ulopyranosonate

methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-talo-non-2-enonate

3-(p-tolyl)allyl-Neu₅Ac₂en 4,5-oxazoline

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