methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

Base Information

Chemical Name:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate
CAS No.:1408294-48-3
Molecular Formula:C₃₂H₃₉NO₁₄
Molecular Weight:661.66
Hs Code.:

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

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Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

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Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

There total 6 articles about methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-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: 94.0%

: 1262101-29-0
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-(prop-2′-enyl)-D-glycero-D-galacto-non-2-enonate

: 272130-84-4
methyl 2-methyl-5-vinylbenzoate

: 1408294-48-3
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 24h; Inert atmosphere;
DOI:10.1039/c2ob25627d

Reference yield:

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 1408294-48-3
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

Guidance literature:: Multi-step reaction with 6 steps

1: N-Bromosuccinimide / dimethyl sulfoxide; water / 2 h / -30 °C

2: 2,2'-azobis(isobutyronitrile) / toluene / 8 h / 100 °C / Inert atmosphere

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

4: acetyl chloride / dichloromethane; methanol / 48 h / 5 - 20 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 16 h / 20 °C / Inert atmosphere

6: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 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; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In methanol; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1039/c2ob25627d

Reference yield:

: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3-bromo-3,5-dideoxy-α-D-erythro-L-gluco-non-2-ulopyranosonate

: 1408294-48-3
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-[3′-(3-methylcarboxy-4-methyl)phenyl-prop-2′-enyl]-D-glycero-D-galacto-non-2-enonate

Guidance literature:: Multi-step reaction with 5 steps

1: 2,2'-azobis(isobutyronitrile) / toluene / 8 h / 100 °C / Inert atmosphere

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

3: acetyl chloride / dichloromethane; methanol / 48 h / 5 - 20 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 16 h / 20 °C / Inert atmosphere

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 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; 2,2'-azobis(isobutyronitrile); 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In methanol; dichloromethane; toluene;
DOI:10.1039/c2ob25627d