methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

Base Information

• Chemical Name: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate
• CAS No.: 120123-59-3
• Molecular Formula: C₂₆H₃₂ClNO₁₂S
• Molecular Weight: 618.059
• Mol file: 120123-59-3.mol

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

There total 2 articles about methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate 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: 77.0%

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + benzenesulfenyl chloride (931-59-9) → (3R,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (120104-58-7,120104-59-8,120104-60-1,120123-59-3) + (3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (120104-58-7,120104-59-8,120104-60-1,120123-59-3)

Guidance literature:

In dichloromethane; at 30 ℃; for 48h;

DOI:10.1246/cl.1988.1657

Reference yield: 77.0%

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + benzenesulfenyl chloride (931-59-9) → (3R,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (120104-58-7,120104-59-8,120104-60-1,120123-59-3) + (3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (120104-58-7,120104-59-8,120104-60-1,120123-59-3)

Guidance literature:

In dichloromethane; at 30 ℃; for 48h;

DOI:10.1246/cl.1988.1657

Reference yield: 96.0%

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate (120123-59-3) → methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate (140484-47-5)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In water; 1,2-dichloro-ethane; at 70 ℃; for 4h;

DOI:10.1016/0008-6215(92)84099-E

upstream raw materials:

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

benzenesulfenyl chloride

Downstream raw materials:

methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid>onate