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

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS No.: 189744-16-9
• Molecular Formula: C₃₂H₄₀O₆Si
• Molecular Weight: 548.751
• Mol file: 189744-16-9.mol

Synonyms:2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-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-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

There total 3 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-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: 95.0%

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside + benzyl bromide (100-39-0) → 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (189744-16-9)

Guidance literature:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 5.5h;

DOI:10.1002/chem.201203865

Reference yield:

C12H26O5Si → 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (189744-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 10-camphorsufonic acid / N,N-dimethyl-formamide / 11 h / 20 - 80 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

2.2: 5.5 h / 0 °C

With 10-camphorsufonic acid; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1002/chem.201203865

Reference yield:

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (81342-44-1) → 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (189744-16-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / methanol; tetrahydrofuran / 2.5 h / 20 °C

2.1: 10-camphorsufonic acid / N,N-dimethyl-formamide / 11 h / 20 - 80 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

3.2: 5.5 h / 0 °C

With 10-camphorsufonic acid; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1002/chem.201203865

upstream raw materials:

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

benzyl bromide

Downstream raw materials:

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside