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

Base Information

• Chemical Name: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER
• CAS No.: 118977-26-7
• Molecular Formula: C₂₆H₃₃NO₁₂S
• Molecular Weight: 583.614
• Mol file: 118977-26-7.mol

Synonyms:PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER;Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thiophenyl-D-glycero-a-D-galacto-2-nonulopyranosylonate;N-Acetyl-2-S-phenyl-2-thio-alpha-neuraminic acid methyl ester 4,7,8,9-tetraacetate

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

Chemical Property:

• Boiling Point: 671.0±55.0 °C(Predicted)
• PKA: 13.79±0.70(Predicted)
• PSA: 195.13000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 1.69070

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thiophenyl-D-glycero-a-D-galacto-2-nonulopyranosylonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Acetyl-?2-?S-?phenyl-?2-?thio-4,?7,?8,?9-?tetraacetate-α-?neuraminic Acid Methyl Ester is a useful reagent for stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid.

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

There total 10 articles about PER-O-ACETYL-ALPHA-THIOPHENYL-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: 81.0%

(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) + thiophenol (108-98-5) → methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate (118977-25-6,118977-26-7) + methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate (118977-25-6)

Guidance literature:

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

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

Reference yield: 80.0%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + thiophenol (108-98-5) → methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate (118977-25-6,118977-26-7)

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

Reference yield: 79.0%

phenylthiotrimethylsilane (4551-15-9) + (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (107020-85-9,107081-02-7,116296-68-5,116296-69-6,129939-94-2,129939-95-3,129939-97-5,129939-98-6) → methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate (118977-25-6,118977-26-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 12.5h;

DOI:10.1039/d1ob00877c

upstream raw materials:

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

thiophenol

(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-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Downstream raw materials:

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

p-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranoside)onate-(2->6)-2-azido-2-deoxy-α-D-galactopyranoside

C₂₂H₂₈Cl₃NO₉S

C₂₄H₂₉Cl₄NO₁₀S

Refernces

• 1、 Dong, Hai,Feng, Guang-Jing,Guo, Yang-Fan,Liu, Chun-Yang,Luo, Tao. "Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions". . . Retrieved 2022/02/07.
• 2、 Shadrick, Melanie,Yu, Charlene,Geringer, Scott,Ritter, Sean,Behm, Alexanndra,Cox, Abby,Lohman, Matt,De Meo, Cristina. "Facile and robust methods for the regioselective acylation of: N -acetylneuraminic acid". supporting information. p. 14138 - 14141. Retrieved 2018/08/28.