(2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid

Base Information

• Chemical Name: (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid
• CAS No.: 4887-11-0
• Molecular Formula: C₂₁H₂₉NO₁₄
• Molecular Weight: 519.46
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID50456018
• Nikkaji Number: J914.842F
• Wikidata: Q82278207
• Mol file: 4887-11-0.mol

Synonyms:4887-11-0;2,4,7,8,9-Penta-O-acetyl N-acetylneuraminic acid;(2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid;SCHEMBL13276331;DTXSID50456018;N-Acetylneuraminic acid 2,4,7,8,9-pentaacetate;2,4,7,8,9-Penta-O-acetylN-acetylneuraminicacid;2-O,4-O,N,7-O,8-O,9-O-Hexaacetyl-beta-neuraminic acid;D-Glycero-D-ido-2-nonulopyranosonicacid,5-(acetylamino)-3,5-dideoxy-,2,4,7,8,9-pentaacetate

Chemical Property of (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid

Chemical Property:

• PSA: 207.13000
• LogP: -0.62690
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 15
• Exact Mass: 519.15880460
• Heavy Atom Count: 36
• Complexity: 901

Purity/Quality:

99% ^*data from raw suppliers

2,4,7,8,9-Penta-O-acetyl N-acetylneuraminic acid ^*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)O)OC(=O)C)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)O)OC(=O)C)OC(=O)C
• Uses: 2,4,7,8,9-Penta-O-acetyl N-acetylneuraminic acid is a neuraminic acid derivative which efficiently rescues muscle phenotype and biochemical defects in mouse models of sialic acid-deficient myopathy.

Technology Process of (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid

There total 2 articles about (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid 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: 72.0%

N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) + acetic anhydride (108-24-7) → N-acetyl-2,4,7,8,9-penta-O-acetyl-D-neuraminic acid (4887-11-0)

Guidance literature:

With 1-ethyl-3-methylimidazolium dicyanamide; at 25 ℃; for 24h;

DOI:10.1039/b200306f

Reference yield:

→ 2,4,7,8,9-Penta-O-acetyl-D-neuraminsaeure (4887-11-0,19342-36-0,72690-20-1,108740-42-7,108740-43-8,108740-44-9)

Guidance literature:

aus N-Acetyl-D-neuraminsaeure und Acetanhydrid in Pyridin (oder in Ggw. von SnCl2);

DOI:10.1007/BF00919154

Reference yield:

N-acetyl-2,4,7,8,9-penta-O-acetyl-D-neuraminic acid (4887-11-0) → (2R,4S,5R,6R)-5-Acetylamino-2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (202194-39-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Ag₂O / dimethylformamide

2: 88 percent / TMSOTf, molecular sieves 4A / 1,2-dichloro-ethane / 6 h / 50 °C

3: NIS/TfOH / 1,2-dimethoxy-ethane / -40 °C

4: NaOH / methanol; H₂O

5: K₂CO₃, drierite / dimethylformamide

6: H₂ / 5percent Pd/CaCO₃ / ethanol

With calcium sulfate; sodium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; potassium carbonate; silver(l) oxide; Lindlar's catalyst; In methanol; 1,2-dimethoxyethane; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)10189-5

upstream raw materials:

N-acetyl neuraminic acid

acetic anhydride

Downstream raw materials:

(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid

(2R,4S,5R,6R)-5-Acetylamino-2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 4887-11-0 N-Acetylneuraminicacid2,4,7,8,9-pentaacetate

Send

Send

Metric Ton KG G Pound L ML

Send

Send