4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside
• CAS No.: 296776-03-9
• Molecular Formula: C32H36O8Si
• Molecular Weight: 576.70894
• Mol file: 296776-03-9.mol

Synonyms:4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside;7-[[6-O-[(1,1-DiMethylethyl)diphenylsilyl]-β-D-galactopyranosyl]oxy]-4-Methyl-2H-1-benzopyran-2-one

Chemical Property of 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside

Chemical Property:

• Melting Point: 168-169 °C
• Boiling Point: 699.0±55.0 °C(Predicted)
• PKA: 12.70±0.70(Predicted)
• PSA: 118.59000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 2.86440
• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

97% ^*data from raw suppliers

4-Methylumbelliferyl6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside can be used as intermediate in the production of fluorescent indicators, used to determine Sulphatase activity.

Technology Process of 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside

There total 5 articles about 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-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%

tert-butylchlorodiphenylsilane (58479-61-1) + 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7,39940-54-0) → 4-methylumbelliferyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside (296776-03-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1039/b613909d

Reference yield:

4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (6160-79-8) → 4-methylumbelliferyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside (296776-03-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; sodium methylate; In methanol; N,N-dimethyl-formamide; 1: Deacetylation / 2: Substitution;

DOI:10.1039/b002754p

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbelliferyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside (296776-03-9)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Substitution;

DOI:10.1039/b002754p

upstream raw materials:

tert-butylchlorodiphenylsilane

4-methylumbelliferyl-β-D-galactopyranoside

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

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

Downstream raw materials:

4-methylumbelliferyl[methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate]-(2->3)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

4-methylumbelliferyl-2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

4-methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside

4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside

Refernces

• 1、 Vankayalapati, Hariprasad,Singh, Gurdial. "Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group". . p. 2187 - 2193. Retrieved 2007/10/03.