2-ACETAMIDO-2-DEOXY-6-O-(ALPHA-L-FUCOPYRANOSYL)-D-GLUCOPYRANOSE

Base Information

• Chemical Name: 2-ACETAMIDO-2-DEOXY-6-O-(ALPHA-L-FUCOPYRANOSYL)-D-GLUCOPYRANOSE
• CAS No.: 33639-80-4
• Molecular Formula: C₁₄H₂₅NO₁₀
• Molecular Weight: 367.353
• Mol file: 33639-80-4.mol

Synonyms:N-[(2R,3S,4R,5S)-2,4,5-Trihydroxy-6-[[(2R,3S,4S,5S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-3-yl]acetamide;

Chemical Property of 2-ACETAMIDO-2-DEOXY-6-O-(ALPHA-L-FUCOPYRANOSYL)-D-GLUCOPYRANOSE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 135-139?C
• Refractive Index: 1.601
• Boiling Point: 736.414 °C at 760 mmHg
• Flash Point: 399.169 °C
• PSA: 178.17000
• Density: 1.558 g/cm³
• LogP: -3.83490
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere

Purity/Quality:

99% ^*data from raw suppliers

2-Acetamido-2-deoxy-6-O-(α-L-fucopyranosyl)-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Oligosaccharide which participates in cell adhesion between bacterial and eukaryotic cells

Technology Process of 2-ACETAMIDO-2-DEOXY-6-O-(ALPHA-L-FUCOPYRANOSYL)-D-GLUCOPYRANOSE

There total 6 articles about 2-ACETAMIDO-2-DEOXY-6-O-(ALPHA-L-FUCOPYRANOSYL)-D-GLUCOPYRANOSE 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: 82.0%

2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-O-α-L-fucopyranosyl-β-D-glucopyranose (81561-95-7) → 2-acetamido-2-deoxy-6-O-α-L-fucopyranosyl-D-glucopyranose (33639-80-4)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/S0008-6215(00)81004-6

Reference yield:

perbenzyl fucosyl bromide (33639-77-9) → 2-acetamido-2-deoxy-6-O-α-L-fucopyranosyl-D-glucopyranose (33639-80-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / tetraethylammonium bromide / dimethylformamide; CH₂Cl₂ / 120 h / Ambient temperature

2: 90 percent / hydrogen / 10percent Pd-C / acetic acid / 48 h

3: 82 percent / sodium methoxide / methanol / Ambient temperature

With hydrogen; sodium methylate; palladium on activated charcoal; tetraethylammonium bromide; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)81004-6

Reference yield:

2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranose (81561-94-6) → 2-acetamido-2-deoxy-6-O-α-L-fucopyranosyl-D-glucopyranose (33639-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / hydrogen / 10percent Pd-C / acetic acid / 48 h

2: 82 percent / sodium methoxide / methanol / Ambient temperature

With hydrogen; sodium methylate; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1016/S0008-6215(00)81004-6

upstream raw materials:

2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-O-α-L-fucopyranosyl-β-D-glucopyranose

perbenzyl fucosyl bromide

2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranose

6-hydroxy-2-acetamido-2-deoxy-1,3,4-tri-O-acetyl-β-D-glucopyranose

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