3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serine

Base Information

• Chemical Name: 3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serine
• CAS No.: 114661-01-7
• Molecular Formula: C₂₂H₃₇N₃O₁₆
• Molecular Weight: 599.546
• Mol file: 114661-01-7.mol

Synonyms:3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serine

Chemical Property of 3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 188°C
• Boiling Point: 1114.3°Cat760mmHg
• Flash Point: 627.7°C
• PSA: 317.12000
• Density: 1.63g/cm³
• LogP: -4.98550
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Purity/Quality:

97% ^*data from raw suppliers

STnEpitope ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sialosyl-Tn epitope is a cancer associated carbohydrate antigen which may be effective as cancer specific targets for immunotherapy as well as in the development of diagnostic monoclonal antibodies. These antigens appear as clusters of glycopeptide repeating units. 3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serines generally contains acetic acid. Sialosyl-Tn epitope is a cancer associated carbohydrate antigen which may be effective as cancer specific targets for immunotherapy as well as in the development of diagnostic monoclonal antibodies. These antigens appear as clusters of glycopeptide repeating units.3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serines generally contains acetic acid.

Technology Process of 3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serine

There total 10 articles about 3-O-(2-acetamido-6-O-(N-acetylneuraminyl)-2-deoxygalactosyl)serine 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:

(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-((S)-2-amino-2-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116246-55-0,116346-46-4) → O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine (114661-01-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(00)90853-X

Reference yield:

Allyl-2-azido-2-desoxy-β-D-galactopyranosid (90405-18-8) → O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine (114661-01-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 41 percent / molecular sives 4A/AgOSO₂CF₃ / tetrahydrofuran / 20 h / 20 °C

2: 98 percent / pyridine / 12 h / 20 °C

3: 79 percent / PdCl₂/AcONa / acetic acid; H₂O / 12 h / 20 °C

4: 70 percent / K₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

5: 82 percent / molecular sives AW/Me₃SiSO₂CF₃ / 1,2-dichloro-ethane / 0.67 h / -15 °C

6: H₂ / Lindlar / methanol / 6.5 h / 40 °C

7: pyridine / 12 h / 20 °C

8: 15 mg / H₂ / 10percent Pd-C / methanol / 3.5 h / 20 °C

9: 10 mg / M aq. NaOH / methanol / 2 h / 20 °C

With sodium hydroxide; molecular sives 4A; molecular sives AW; hydrogen; sodium acetate; silver trifluoromethanesulfonate; potassium carbonate; trimethyl((trifluoromethyl)sulfonyl)silane; palladium dichloride; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(00)90853-X

Reference yield:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine (114661-01-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 41 percent / molecular sives 4A/AgOSO₂CF₃ / tetrahydrofuran / 20 h / 20 °C

2: 98 percent / pyridine / 12 h / 20 °C

3: 79 percent / PdCl₂/AcONa / acetic acid; H₂O / 12 h / 20 °C

4: 70 percent / K₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

5: 82 percent / molecular sives AW/Me₃SiSO₂CF₃ / 1,2-dichloro-ethane / 0.67 h / -15 °C

6: H₂ / Lindlar / methanol / 6.5 h / 40 °C

7: pyridine / 12 h / 20 °C

8: 15 mg / H₂ / 10percent Pd-C / methanol / 3.5 h / 20 °C

9: 10 mg / M aq. NaOH / methanol / 2 h / 20 °C

With sodium hydroxide; molecular sives 4A; molecular sives AW; hydrogen; sodium acetate; silver trifluoromethanesulfonate; potassium carbonate; trimethyl((trifluoromethyl)sulfonyl)silane; palladium dichloride; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(00)90853-X

upstream raw materials:

(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-((S)-2-amino-2-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Allyl-2-azido-2-desoxy-β-D-galactopyranosid

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

allyl O--(2->6)-3,4-di-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

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