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

Base Information

• Chemical Name: methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
• CAS No.: 1453411-79-4
• Molecular Formula: C₂₄H₃₁N₃O₁₃
• Molecular Weight: 569.522

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

Chemical Property of methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

There total 5 articles about methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)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: 83.0%

methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-D-glycero-β-D-galactonon-2-ulopyranosid)onate (1453411-78-3) → methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (1453411-79-4)

Guidance literature:

methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-D-glycero-β-D-galactonon-2-ulopyranosid)onate; With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 12h;

With water; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ja405916q

Reference yield:

(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 (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) → methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (1453411-79-4)

Guidance literature:

Multi-step reaction with 5 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

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; ethyl acetate; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja405916q

Reference yield:

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 (163860-77-3) → methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (1453411-79-4)

Guidance literature:

Multi-step reaction with 2 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

With N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja405916q

upstream raw materials:

(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

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

methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-D-glycero-β-D-galactonon-2-ulopyranosid)onate

methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

Downstream raw materials:

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

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

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

methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

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