4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester

Base Information

• Chemical Name: 4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester
• CAS No.: 84380-10-9
• Molecular Formula: C20H29 N O13
• Molecular Weight: 491.449
• DSSTox Substance ID: DTXSID10456014
• Nikkaji Number: J1.236.212I
• Wikidata: Q82278203
• Mol file: 84380-10-9.mol

Synonyms:84380-10-9;4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester;methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-hydroxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate;N-Acetylneuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate;SCHEMBL3698732;4,7,8,9-Tetra-O-acetyl-D-neuraminic acid methyl ester;DTXSID10456014;CS-0226056;T71380;methyl4,7,8,9-tetra-O-acetyl-N-acetylneuraminate;W-203914;Methyl 4,7,8,9-tetra-O-acetyl-N-acetylneuraminate, 95%;4-O,N,7-O,8-O,9-O-Pentaacetyl-beta-neuraminic acid methyl ester;(1S,2R)-1-((2R,3R,4S,6S)-3-Acetamido-4-acetoxy-6-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate;Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonate

Chemical Property of 4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 185-189°C
• Boiling Point: 581.736oC at 760 mmHg
• PKA: 10.15±0.70(Predicted)
• Flash Point: 305.623oC
• PSA: 190.06000
• Density: 1.348g/cm3
• LogP: -1.10930
• Storage Temp.: Freezer
• Solubility.: slightly sol. in Chloroform
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 14
• Exact Mass: 491.16388998
• Heavy Atom Count: 34
• Complexity: 812

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,7,8,9-Tetra-O-acetyl-N-acetyl-D-neuraminic acid methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(CC(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)O)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)O)OC(=O)C
• Uses: Versatile acetylated neuraminic acid or sialic acid derivative. N-acetylneuraminic acid is often present as the terminal sugar of glycoproteins.

Technology Process of 4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester

There total 18 articles about 4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid 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: 95.0%

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) + acetic anhydride (108-24-7) → 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester (84380-10-9)

Guidance literature:

With lithium perchlorate; at 40 ℃;

DOI:10.1080/07328300600770469

Reference yield: 90.0%

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) + acetic anhydride (108-24-7) → methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl)onate (20298-34-4,84380-10-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 0 - 27 ℃; for 4h;

DOI:10.1016/j.carres.2008.01.014

Reference yield: 87.0%

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl chloride (132883-18-2) → 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester (84380-10-9)

Guidance literature:

With silver carbonate; In water; acetone; for 72h;

DOI:10.1016/S0040-4020(97)00370-0

upstream raw materials:

potassium thioacyanate

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

N-acetylneuraminic acid methyl ester

acetic anhydride

Downstream raw materials:

dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite

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

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

methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Refernces

• 1、 Lin, Ting-Wei,Adak, Avijit K.,Lin, Hong-Jyune,Das, Anindya,Hsiao, Wei-Chen,Kuan, Ting-Chun,Lin, Chun-Cheng. "Tetranuclear zinc cluster: A dual purpose catalyst for per-: O -acetylation and de- O -acetylation of carbohydrates". . p. 58749 - 58754. Retrieved 2016/07/07.
• 2、 -. "NOVEL GLYCOSYL PHOSPHITES". Page/Page column 15. . Retrieved 2012/09/11.