PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER

Base Information

• Chemical Name: PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER
• CAS No.: 121512-91-2
• Molecular Formula: C22H33 N O12 S
• Molecular Weight: 535.57
• Mol file: 121512-91-2.mol

Synonyms:D-glycero-a-D-galacto-2-Nonulopyranosidonicacid, ethyl 5-(acetylamino)-3,5-dideoxy-2-thio-, methyl ester,4,7,8,9-tetraacetate

Chemical Property of PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER

Chemical Property:

• PSA: 195.13000
• LogP: 0.65150

Purity/Quality:

95% ^*data from raw suppliers

PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER

There total 13 articles about PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER 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: 96.0%

(2S,4S,5R,6R)-5-Acetylamino-2-ethylsulfanyl-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (145387-36-6) + acetic anhydride (108-24-7) → methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (121512-91-2)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1055/s-2005-868514

Reference yield: 72.0%

(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) + ethanethiol (75-08-1) → methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (121512-91-2) + methyl (ethyl 5-acetoamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (121512-90-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(89)80054-0

Reference yield: 62.0%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + ethanethiol (75-08-1) → methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (121512-91-2)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In ethyl acetate; for 1h; Ambient temperature;

DOI:10.1016/S0957-4166(00)86308-9

upstream raw materials:

O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate

(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

ethanethiol

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

Downstream raw materials:

benzyl O--(2-3)-2,6-di-O-benzyl-β-D-galactopyranoside

benzyl O--(2-3)-2,6-di-O-benzyl-β-D-galactopyranoside

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

methyl [(3-trifluoroacetamidopropyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-pyranoside]-2-nonulosonate