methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate
• CAS No.: 1449035-92-0
• Molecular Formula: C₂₈H₃₄N₄O₁₀
• Molecular Weight: 586.599

Synonyms:methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Chemical Property of methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

There total 8 articles about methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-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: 85.0%

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 (1449035-90-8) → methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate (1449035-92-0)

Guidance literature:

With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 5 - 20 ℃; for 7.25h; Inert atmosphere;

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-(prop-2'-enyl)-α/β-D-erythro-L-gluco-non-2-ulopyranosonate → methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate (1449035-92-0)

Guidance literature:

Multi-step reaction with 5 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: diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 7.25 h / 5 - 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; ethyl acetate; benzene;

DOI:10.1016/j.bmc.2013.05.054

Reference yield:

1-ethenyl-4-methylbenzene (622-97-9,24936-41-2) → methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate (1449035-92-0)

Guidance literature:

Multi-step reaction with 5 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: diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 7.25 h / 5 - 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; ethyl acetate; benzene;

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

Downstream raw materials:

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

methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

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

methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

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