4-Methylumbelliferyl 3-O-(a-L-fucopyranosyl)-b-D-galactopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl 3-O-(a-L-fucopyranosyl)-b-D- galactopyranoside
• CAS No.: 296776-06-2
• Molecular Formula: C₂₂H₂₈O₁₂
• Molecular Weight: 484.457
• Mol file: 296776-06-2.mol

Synonyms:4-Methylumbelliferyl 3-O-(a-L-fucopyranosyl)--D-galactopyranoside;4-Methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside;7-[[3-O-(6-Deoxy-α-L-galactopyranosyl)-β-D-galactopyranosyl]oxy]-4-Methyl-2H-1-benzopyran-2-one;Fuc1-α-3Gal1-b-4-MU;7-[[3-O-(6-Deoxy-alpha-L-galactopyranosyl)-beta-D-galactopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one

Chemical Property of 4-Methylumbelliferyl 3-O-(a-L-fucopyranosyl)-b-D-galactopyranoside

Chemical Property:

• Vapor Pressure: 1.1E-26mmHg at 25°C
• Boiling Point: 795.4°C at 760 mmHg
• PKA: 12.52±0.70(Predicted)
• Flash Point: 274.9°C
• PSA: 188.51000
• Density: 1.58g/cm³
• LogP: -1.86810

Purity/Quality:

98% ^*data from raw suppliers

4-Methylumbelliferyl3-O-(α-L-Fucopyranosyl)-β-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Methylumbelliferyl 3-O-(a-L-fucopyranosyl)-b-D-galactopyranoside

There total 10 articles about 4-Methylumbelliferyl 3-O-(a-L-fucopyranosyl)-b-D-galactopyranoside 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: 87.0%

4-methylumbelliferyl 3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside (296776-05-1) → 4-methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside (296776-06-2)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.5h;

DOI:10.1039/b002754p

Reference yield:

4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (6160-79-8) → 4-methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside (296776-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / NaOMe / methanol / 0.5 h / 20 °C

2: 79 percent / imidazole / dimethylformamide / 8 h / 20 °C

3: 27 percent / Et₄NBr; molecular sieves 4 Angstroem / CH₂Cl₂ / 48 h / 20 °C

4: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

5: 87 percent / NaOMe; MeOH / 0.5 h / 20 °C

With 1H-imidazole; methanol; 4 A molecular sieve; tetraethylammonium bromide; tetrabutyl ammonium fluoride; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: Substitution / 3: Substitution / 4: Desilylation / 5: Deacetylation;

DOI:10.1039/b002754p

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside (296776-06-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -78 °C

2: 83 percent / NaOMe / methanol / 0.5 h / 20 °C

3: 79 percent / imidazole / dimethylformamide / 8 h / 20 °C

4: 27 percent / Et₄NBr; molecular sieves 4 Angstroem / CH₂Cl₂ / 48 h / 20 °C

5: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

6: 87 percent / NaOMe; MeOH / 0.5 h / 20 °C

With 1H-imidazole; methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetraethylammonium bromide; tetrabutyl ammonium fluoride; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Substitution / 4: Substitution / 5: Desilylation / 6: Deacetylation;

DOI:10.1039/b002754p

upstream raw materials:

4-methylumbelliferyl 3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside

4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide

7-hydroxy-4-methyl-chromen-2-one

Refernces