5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

Base Information

• Chemical Name: 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate
• CAS No.: 156726-98-6
• Molecular Formula: C28H35NO14S
• Molecular Weight: 641.6408
• Mol file: 156726-98-6.mol

Synonyms:5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

Chemical Property of 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 706.596°C at 760 mmHg
• Flash Point: 381.136°C
• PSA: 221.43000
• Density: 1.352g/cm³
• LogP: 1.23230

Purity/Quality:

99% ^*data from raw suppliers

5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonicAcidMethylEster2,4,7,8,9-Pentaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

There total 6 articles about 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate 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:

acetic anhydride (108-24-7) + (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-hydroxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester → Methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-3-(phenylthio)-D-erythro-β-L-gluco-2-nonulopyranosonate (156726-98-6)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h; Yield given;

DOI:10.1039/c39940000831

Reference yield:

mercury(II) diacetate (1600-27-7) + (2S,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) → Methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-3-(phenylthio)-D-erythro-β-L-gluco-2-nonulopyranosonate (156726-98-6) + Methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-3-(phenylthio)-D-erythro-α-L-gluco-2-nonulopyranosonate

Guidance literature:

With acetic anhydride; acetic acid; at 40 ℃; for 18h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00116a022

Reference yield:

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) → Methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-3-(phenylthio)-D-erythro-β-L-gluco-2-nonulopyranosonate (156726-98-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / CH₂Cl₂ / 168 h / 20 °C

2: HgBr₂, Hg(CN)2 / 1,2-dichloro-ethane; H₂O / 3.5 h / Heating

3: pyridine, DMAP / 1 h / 20 °C

With pyridine; dmap; mercury(II) cyanide; mercury dibromide; In dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1039/c39940000831

upstream raw materials:

acetic anhydride

(2S,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

mercury(II) diacetate

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

Downstream raw materials:

Methyl onate

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