2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside
• CAS No.: 299424-55-8
• Molecular Formula: C₆₇H₇₈O₁₂Si
• Molecular Weight: 1103.43
• Mol file: 299424-55-8.mol

Synonyms:2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside

There total 7 articles about 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside 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: 97.9%

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (74801-29-9) + 2-(trimethylsilyl)ethyl 2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside (299424-48-9) → 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside (299424-55-8)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -40 ℃; for 0.5h;

DOI:10.1248/cpb.48.1160

Reference yield:

2-(trimethylsilyl)ethyl β-D-galactopyranoside (117252-95-6) → 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside (299424-55-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dibutyltin oxide / methanol / 2 h / Heating

1.2: 66.9 percent / CsF / dimethylformamide / 5 h

2.1: imidazole / dimethylformamide / 3 h / 20 °C

3.1: 605 mg / NaH / dimethylformamide / 4 h / 0 °C

4.1: 81.7 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

5.1: 97.9 percent / 4A MS; NIS; TfOH / CH₂Cl₂; acetonitrile / 0.5 h / -40 °C

With 1H-imidazole; N-iodo-succinimide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.48.1160

Reference yield:

benzyl bromide (100-39-0) → 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside (299424-55-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 605 mg / NaH / dimethylformamide / 4 h / 0 °C

2: 81.7 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

3: 97.9 percent / 4A MS; NIS; TfOH / CH₂Cl₂; acetonitrile / 0.5 h / -40 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.48.1160

upstream raw materials:

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

2-(trimethylsilyl)ethyl 2,4-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside

2-(trimethylsilyl)ethyl β-D-galactopyranoside

benzyl bromide

Downstream raw materials:

2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-benzyl-β-D-galactopyranoside