methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate

Base Information

Chemical Name:methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate
CAS No.:1453411-88-5
Molecular Formula:C₁₉H₂₆N₂O₁₁
Molecular Weight:458.422
Hs Code.:

Synonyms:methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate

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Chemical Property of methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate

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Technology Process of methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate

There total 7 articles about methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate 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: 32.0%

: 100-02-7,78813-13-5,89830-32-0
4-nitro-phenol

: 439801-65-7
methyl (5-acetamido-3,4,5-trideoxy-7,8,9-tri-O-acetyl-4-methoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate chloride

: 1453411-88-5
methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate

: 1453411-89-6
methyl (5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-methoxy-D-glycero-D-galacto-non-2-en)onate

Guidance literature:: 4-nitro-phenol; methyl (5-acetamido-3,4,5-trideoxy-7,8,9-tri-O-acetyl-4-methoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate chloride; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20 ℃; for 48h;

With sodium methylate; In methanol; at 0 ℃; for 0.5h;

In methanol;
DOI:10.1021/ja405916q

Reference yield:

: 19342-33-7
N-acetyl neuraminic acid

: 1453411-88-5
methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate

Guidance literature:: Multi-step reaction with 7 steps

1.1: Amberlite IR-120 resin (H⁺form) / 48 h / Reflux

2.1: toluene-4-sulfonic acid / 4 h / 20 °C / Molecular sieve

3.1: sodium hydride / acetonitrile / 0.25 h / 0 °C / Inert atmosphere

3.2: 0.33 h / 0 °C / Inert atmosphere

4.1: sodium hydroxide / water; methanol / 1 h / 20 °C

4.2: Amberlite IR-120 resin (H⁺ form) / 70 °C

5.1: 3 h / 20 °C / Inert atmosphere

6.1: acetyl chloride; acetic acid / methanol / 48 h / 0 - 20 °C / Sealed tube

7.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 48 h / 0 - 20 °C

7.2: 0.5 h / 0 °C

7.3: Amberlite IR-120 resin (H⁺ form)

With sodium hydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; acetyl chloride; sodium hydroxide; In methanol; water; acetonitrile;
DOI:10.1021/ja405916q

Reference yield:

: 1104460-84-5
methyl (5-acetamido-3,4,5-trideoxy-4-methoxy-D-glycero-β-D-galacto-non-2-ulopyranosid)onate

: 1453411-88-5
methyl (4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-methoxy-β-D-glycero-D-galacto-non-2-ulpyranosid)onate

Guidance literature:: Multi-step reaction with 2 steps

1.1: acetyl chloride; acetic acid / methanol / 48 h / 0 - 20 °C / Sealed tube

2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 48 h / 0 - 20 °C

2.2: 0.5 h / 0 °C

2.3: Amberlite IR-120 resin (H⁺ form)

With acetic acid; N-ethyl-N,N-diisopropylamine; acetyl chloride; In methanol; acetonitrile;
DOI:10.1021/ja405916q