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

Base Information

• Chemical Name: 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
• CAS No.: 569650-75-5
• Molecular Formula: C₆₈H₈₂O₁₇Si
• Molecular Weight: 1199.47
• Mol file: 569650-75-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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: 80.0%

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 (569650-74-4) → 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:

With palladium dichloride; In methanol; at 20 ℃; for 3h;

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

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) → 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: 74 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.75 h / -10 °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; acetic acid; palladium dichloride; In methanol; dichloromethane; acetone;

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

Reference yield:

benzyl bromide (100-39-0) → 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 6 steps

1.1: 90 percent / NaH / dimethylformamide / 6 h / 20 °C

2.1: 79 percent / NaCNBH₃; TFA / dimethylformamide / 7 h / 20 °C

3.1: 70 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.75 h / -10 °C

4.1: 80 percent / aq. AcOH / 4 h / 80 °C

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

5.2: 63 percent / CH₂Cl₂; diethyl ether

6.1: 80 percent / PdCl₂ / methanol / 3 h / 20 °C

With chromium(VI) oxide; N-iodo-succinimide; trifluorormethanesulfonic acid; sulfuric acid; sodium hydride; 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:

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

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

benzyl bromide

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

C₁₁₀H₁₂₆O₂₇Si