tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate

Base Information

• Chemical Name: tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate
• CAS No.: 876405-36-6
• Molecular Formula: C₅₁H₆₄O₁₃Si
• Molecular Weight: 913.147
• Mol file: 876405-36-6.mol

Synonyms:tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate

Chemical Property of tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate

There total 6 articles about tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate 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: 71.0%

tert-butyl alcohol (75-65-0) + 2-(trimethylsilyl)ethyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-β-D-glucopyranoside (876405-35-5) → tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate (876405-36-6)

Guidance literature:

With dipyridinium dichromate; acetic anhydride; In dichloromethane; at 0 ℃; for 4h;

Reference yield:

ethyl 2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (454664-78-9) → tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate (876405-36-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / pyridine

2: 71.4 percent / mercury(II) trifluoroacetate / CH₂Cl₂; H₂O / 12 h / 0 °C

3: 69.2 percent / K₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

4: 69 percent / TESOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h / -35 °C

5: 68 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 4 h / 25 °C

6: 71 percent / Ac₂O; pyridinium dichromate / CH₂Cl₂ / 4 h / 0 °C

With pyridine; dipyridinium dichromate; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; mercury(II) trifluoroacetate; acetic anhydride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

Reference yield:

ethyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (521309-20-6) → tert-butyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate (876405-36-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 71.4 percent / mercury(II) trifluoroacetate / CH₂Cl₂; H₂O / 12 h / 0 °C

2: 69.2 percent / K₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

3: 69 percent / TESOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h / -35 °C

4: 68 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 4 h / 25 °C

5: 71 percent / Ac₂O; pyridinium dichromate / CH₂Cl₂ / 4 h / 0 °C

With dipyridinium dichromate; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; mercury(II) trifluoroacetate; acetic anhydride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

upstream raw materials:

tert-butyl alcohol

2-(trimethylsilyl)ethyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-β-D-glucopyranoside

ethyl 2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

ethyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

tert-butyl 2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate