p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside
• CAS No.: 323195-43-3
• Molecular Formula: C₄₈H₅₀O₉SSi
• Molecular Weight: 831.071
• Mol file: 323195-43-3.mol

Synonyms:p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside

Chemical Property of p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside

There total 8 articles about p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside 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: 88.1%

levulinic acid (123-76-2) + p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside (323195-42-2) → p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside (323195-43-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/jccs.200000125

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside (323195-43-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 85.3 percent / BF₃*Et₂O / CH₂Cl₂ / 20 °C

2: NaOMe; MeOH / 2 h / 20 °C

3: 76.5 percent / p-TsOH*H₂O / acetonitrile

4: 77.4 percent / pyridine / CH₂Cl₂ / 20 °C

5: 89.5 percent / 80 percent aq. AcOH / 3 h / 90 °C

6: 96.6 percent / imidazole / dimethylformamide / 1 h / 20 °C

7: 88.1 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; methanol; dmap; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/jccs.200000125

Reference yield:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) → p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside (323195-43-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 76.5 percent / p-TsOH*H₂O / acetonitrile

2: 77.4 percent / pyridine / CH₂Cl₂ / 20 °C

3: 89.5 percent / 80 percent aq. AcOH / 3 h / 90 °C

4: 96.6 percent / imidazole / dimethylformamide / 1 h / 20 °C

5: 88.1 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/jccs.200000125

upstream raw materials:

levulinic acid

p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside

D-glucose pentaacetate

p-methylphenyl 1-thio-β-D-glucopyranoside