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

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside
• CAS No.: 117253-11-9
• Molecular Formula: C₂₅H₃₄O₆Si
• Molecular Weight: 458.627
• Mol file: 117253-11-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside

There total 6 articles about 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-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: 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:

2-(Trimethylsilyl)ethanol (2916-68-9) → 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside (117253-11-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / HgO, HgBr₂, CaSO₄ / CHCl₃ / 48 h / Ambient temperature

2: 90 percent / CH₃ONa / methanol / 3 h

3: 83 percent / p-TsOH*H₂O / tetrahydrofuran / 27 h / 22 °C

4: 27 percent / t-Bu₄NHSO₄, 1.3 M aq. NaOH / CH₂Cl₂ / 48 h / Heating

With calcium sulfate; sodium hydroxide; sodium methylate; toluene-4-sulfonic acid; tetra-tert-butylammonium hydrogen sulfate; mercury dibromide; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1021/jo00259a006

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside (117253-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / p-TsOH*H₂O / tetrahydrofuran / 27 h / 22 °C

2: 27 percent / t-Bu₄NHSO₄, 1.3 M aq. NaOH / CH₂Cl₂ / 48 h / Heating

With sodium hydroxide; toluene-4-sulfonic acid; tetra-tert-butylammonium hydrogen sulfate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00259a006

upstream raw materials:

benzyl bromide

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

2-(Trimethylsilyl)ethanol

benzaldehyde dimethyl acetal

Downstream raw materials:

2-(trimethylsilyl)ethyl 2-O-benzyl-β-D-glucopyranoside

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

3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl chloride

3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl chloride