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

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside
• CAS No.: 569650-70-0
• Molecular Formula: C₃₃H₄₂O₇Si
• Molecular Weight: 578.778
• Mol file: 569650-70-0.mol

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

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

There total 1 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-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: 90.0%

benzyl bromide (100-39-0) + 2-(trimethylsilyl)ethyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside → 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside (569650-70-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1016/S0008-6215(02)00499-8

Reference yield: 79.0%

2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside (569650-70-0) → 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (569650-71-1)

Guidance literature:

With sodium cyanoborohydride; trifluoroacetic acid; In N,N-dimethyl-formamide; at 20 ℃; for 7h;

DOI:10.1016/S0008-6215(02)00499-8

Reference yield:

2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside (569650-70-0) → methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate (569650-75-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / NaCNBH₃; TFA / dimethylformamide / 7 h / 20 °C

2.1: 70 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.75 h / -10 °C

3.1: 80 percent / aq. AcOH / 4 h / 80 °C

4.1: CrO₃; aq. H₂SO₄ / acetone; CH₂Cl₂ / 9.25 h / 0 - 20 °C

4.2: 63 percent / CH₂Cl₂; diethyl ether

5.1: 80 percent / PdCl₂ / methanol / 3 h / 20 °C

With chromium(VI) oxide; N-iodo-succinimide; trifluorormethanesulfonic acid; sulfuric acid; sodium cyanoborohydride; acetic acid; trifluoroacetic acid; palladium dichloride; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(02)00499-8

upstream raw materials:

benzyl bromide

Downstream raw materials:

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

methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid]uronate

acetic acid 4-allyloxy-6-benzyloxymethyl-2-[4,5-bis-benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate