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.: 117253-04-0
• Molecular Formula: C₃₂H₄₀O₆Si
• Molecular Weight: 548.751
• Mol file: 117253-04-0.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 7 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: 82.0%

benzyl chloride (100-44-7) + 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside (117253-03-9) → 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (117253-04-0)

Guidance literature:

With potassium hydroxide; In toluene; for 15h; Heating;

DOI:10.1021/jo00259a006

Reference yield: 18.0%

benzyl bromide (100-39-0) + 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside (117253-03-9) → 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside (117253-11-9) + 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (117253-04-0) + 2-(trimethylsilyl)ethyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (117253-10-8)

Guidance literature:

With sodium hydroxide; tetra-tert-butylammonium hydrogen sulfate; In dichloromethane; for 48h; Heating;

DOI:10.1021/jo00259a006

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (117253-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / PTSA / acetonitrile / 3 h / 25 °C

2: 1.) NaH / 1.) DMF, 20 deg C, 2 h, 2.) 25 deg C, 3 h

With sodium hydride; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1021/jo951067l

upstream raw materials:

benzyl bromide

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

benzyl chloride

benzaldehyde dimethyl acetal

Downstream raw materials:

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

2-(Trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside