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

Base Information

Chemical Name: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
CAS No.:1449035-90-8
Molecular Formula:C₂₈H₃₅NO₁₁
Molecular Weight:561.586
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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: 96.0%

: 1449035-88-4
3-(p-tolyl)allyl-Neu₅Ac₂en 4,5-oxazoline

: 1449035-90-8
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

Guidance literature:: With water; trifluoroacetic acid; In ethyl acetate; at 20 ℃; for 16h;
DOI:10.1016/j.bmc.2013.05.054

Reference yield:

: 622-97-9,24936-41-2
1-ethenyl-4-methylbenzene

: 1449035-90-8
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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; trimethylsilyl trifluoromethanesulfonate; water; trifluoroacetic acid; In dichloromethane; 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

: 1449035-90-8
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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; water; trifluoroacetic acid; In ethyl acetate;
DOI:10.1016/j.bmc.2013.05.054