4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid

Base Information

Chemical Name:4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid
CAS No.:1453411-72-7
Molecular Formula:C₁₉H₂₇N₃O₁₀
Molecular Weight:457.437
Hs Code.:

Synonyms:4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid

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Chemical Property of 4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid

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Technology Process of 4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid

There total 7 articles about 4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic 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: 45.0%

: 1453411-82-9
methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

: 1453411-72-7
4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid

Guidance literature:: methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate; With sodium methylate; In methanol; at 0 ℃; for 0.5h;

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

In tetrahydrofuran; water;
DOI:10.1021/ja405916q

Reference yield:

: 163860-77-3
methyl (5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate chloride

: 1453411-72-7
4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 0 - 20 °C

2.1: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C

2.2: 24 h / 20 °C

3.1: methanol / 2 h / 20 °C

4.1: sodium methylate / methanol / 0.5 h / 0 °C

4.2: 0.5 h / 0 °C

4.3: Amberlite IR-120 resin (NH₄⁺ form

With sodium methylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1021/ja405916q

Reference yield:

: 108740-39-2,6931-68-6,72690-21-2,73208-82-9,108740-37-0,108740-38-1,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,74006-95-4
(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

: 1453411-72-7
4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 50 °C / Inert atmosphere

2.1: trimethylsilylazide / tert-butyl alcohol / 12 h / 80 °C / Inert atmosphere

3.1: lithium chloride / 2 h / 0.2 Torr / Molecular sieve

4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 0 - 20 °C

5.1: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C

5.2: 24 h / 20 °C

6.1: methanol / 2 h / 20 °C

7.1: sodium methylate / methanol / 0.5 h / 0 °C

7.2: 0.5 h / 0 °C

7.3: Amberlite IR-120 resin (NH₄⁺ form

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; sodium methylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; methanol; ethyl acetate; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja405916q