methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Base Information

• Chemical Name: methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• CAS No.: 124974-13-6
• Molecular Formula: C₂₆H₃₂N₂O₁₄S
• Molecular Weight: 628.611
• Mol file: 124974-13-6.mol

Synonyms:methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Chemical Property of methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

There total 3 articles about methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)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: 81.0%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + para-nitrobenzenethiol (1849-36-1) → methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (124974-13-6)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; at 25 ℃;

Reference yield:

N-acetylneuraminic acid methyl ester (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2) → methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (124974-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 h / 20 °C

2: tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate / ethyl acetate / 3 h / 20 °C

With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In ethyl acetate;

DOI:10.1016/j.carres.2009.08.034

Reference yield:

N-acetyl neuraminic acid (19342-33-7) → methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (124974-13-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Amberlite IR-120 / 48 h / 20 °C / Inert atmosphere

2: 72 h / 20 °C

3: tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate / ethyl acetate / 3 h / 20 °C

With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In ethyl acetate;

DOI:10.1016/j.carres.2009.08.034

upstream raw materials:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

para-nitrobenzenethiol

N-acetylneuraminic acid methyl ester

N-acetyl neuraminic acid

Downstream raw materials:

4-N-acetamidophenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid) onate

(2S,4S,5R,6R)-5-Acetylamino-2-(4-acryloylamino-phenylsulfanyl)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

(2S,4S,5R,6R)-5-Acetylamino-2-(4-acryloylamino-phenylsulfanyl)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(4-acryloylamino-phenylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester