2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside
• CAS No.: 904319-27-3
• Molecular Formula: C₃₃H₄₂O₈Si
• Molecular Weight: 594.777
• Mol file: 904319-27-3.mol

Synonyms:2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside

There total 1 articles about 2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-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:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside + benzoyl chloride (98-88-4) + p-methoxybenzyl chloride (824-94-2) → 2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside (904319-27-3) + Benzoic acid (2R,3R,4S,5R,6R)-2-benzyloxymethyl-3-hydroxy-5-(4-methoxy-benzyloxy)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:

Multistep reaction;

DOI:10.1016/j.carres.2006.04.019

Reference yield: 57.0%

phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside (904319-28-4) + 2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside (904319-27-3) → 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-β-D-glucopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzoyl-β-D-glucopyranoside (904319-29-5)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -40 ℃;

DOI:10.1016/j.carres.2006.04.019

Reference yield:

2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside (904319-27-3) → 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-β-D-glucopyranoside (904319-32-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; 4 Angstroem molecular sieves / CH₂Cl₂ / -40 °C

2: 77 percent / NaHCO₃ / methanol; H₂O; tetrahydrofuran / 1 h / 50 °C

3: CH₂Cl₂; pyridine / 2 h / -20 - 0 °C

4: 501 mg / dimethylformamide / 2.5 h / 20 - 100 °C

5: 78 percent / DDQ / CH₂Cl₂; H₂O / 10 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.04.019

upstream raw materials:

benzoyl chloride

p-methoxybenzyl chloride

Downstream raw materials:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-β-D-glucopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzoyl-β-D-glucopyranoside

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

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-3-O-benzyl-β-D-glucopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzoyl-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside