2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside
• CAS No.: 904319-34-2
• Molecular Formula: C₅₁H₆₆O₂₄Si
• Molecular Weight: 1091.16
• Mol file: 904319-34-2.mol

Synonyms:2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside

There total 1 articles about 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-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: 100.0%

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-benzyl-β-D-glucopyranoside (904319-33-1) + acetic anhydride (108-24-7) → 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside (904319-34-2)

Guidance literature:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-benzyl-β-D-glucopyranoside; With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid; at 20 ℃; for 3h;

acetic anhydride; In pyridine;

DOI:10.1016/j.carres.2006.04.019

Reference yield: 86.0%

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside (904319-34-2) + trichloroacetonitrile (545-06-2) → 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-α-D-glucopyranosyl trichloroacetimidate (904319-35-3)

Guidance literature:

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2.5h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.carres.2006.04.019

Reference yield:

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside (904319-34-2) → 6-aminohexyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyanosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside (904319-38-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CF₃CO₂H / CH₂Cl₂ / 2.5 h / 0 - 20 °C

1.2: 86 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

2.1: 100 percent / AW₃₀₀ molecular sieves; TMSOTf / CH₂Cl₂ / 4 h / 0 °C

3.1: 100 percent / HOAc; zinc powder / 16 h / 20 °C

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; acetic acid; trifluoroacetic acid; zinc; In dichloromethane;

DOI:10.1016/j.carres.2006.04.019

upstream raw materials:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-benzyl-β-D-glucopyranoside

acetic anhydride

Downstream raw materials:

3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-α-D-glucopyranosyl trichloroacetimidate

6-aminohexyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyanosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside

6-N-(2,2,2-trichloroethoxycarbonyl)aminohexyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside

C₆₂H₈₂N₂O₂₉