2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside
• CAS No.: 176095-80-0
• Molecular Formula: C₅₃H₅₆O₁₆Si
• Molecular Weight: 977.104
• Mol file: 176095-80-0.mol

Synonyms:2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside

There total 5 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-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: 16.0%

2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-4,6-O-(p-methoxybenzylidene)-β-D-galactopyranosyl>-β-D-glucopyranoside → 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-4-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside + 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside (176095-80-0)

Guidance literature:

With water; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 80 ℃; for 20h;

DOI:10.1021/jo952177v

Reference yield:

2-(trimethylsilyl)ethyl 4-O-(4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside (160533-98-2) → 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside (176095-80-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / I₁, imidazole, PPh₃ / toluene; acetonitrile / 5 h / Heating

2: 92 percent / H₂ / Pd/C / ethyl acetate; ethanol; triethylamine / 3 h

3: 91 percent / DMAP / pyridine / Ambient temperature; overnight

4: 66 percent / DDQ, AcOH / toluene / 80 °C / overnight83

With 1H-imidazole; dmap; hydrogen; acetic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In pyridine; ethanol; ethyl acetate; triethylamine; toluene; acetonitrile;

DOI:10.1021/jo951914k

Reference yield:

2-(trimethylsilyl)ethyl 6-deoxy-6-iodo-4-O-<4,6-O-(p-methoxybenzylidene)-β-D-galactopyranosyl>-β-D-glucopyranoside → 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside (176095-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / H₂ / Pd/C / ethyl acetate; ethanol; triethylamine / 3 h

2: 91 percent / DMAP / pyridine / Ambient temperature; overnight

3: 66 percent / DDQ, AcOH / toluene / 80 °C / overnight83

With dmap; hydrogen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In pyridine; ethanol; ethyl acetate; triethylamine; toluene;

DOI:10.1021/jo951914k

upstream raw materials:

benzoyl chloride

2-(trimethylsilyl)ethyl 4-O-(4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside