methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

Base Information

• Chemical Name: methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
• CAS No.: 858129-92-7
• Molecular Formula: C₄₉H₆₂O₁₂SSi
• Molecular Weight: 903.176
• Mol file: 858129-92-7.mol

Synonyms:

Chemical Property of methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

There total 8 articles about methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 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: 49.0%

methyl 4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (858129-88-1) + 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl bromide (858129-90-5) → methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (858129-92-7)

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1135/cccc20041768

Reference yield:

methyl 1-thio-β-L-fucopyranoside (114853-38-2) → methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (858129-92-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: p-TsOH / CH₂Cl₂

2.1: NaH / dimethylformamide / 0.33 h

2.2: dimethylformamide

3.1: 98 percent / aq. AcOH / CH₂Cl₂

4.1: 63 percent / imidazole / dimethylformamide / 20 °C

5.1: 75 percent / CuBr₂; 4 Angstroem molecular sieves / CH₂Cl₂

6.1: 49 percent / Bu₄NBr; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide

With 1H-imidazole; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; toluene-4-sulfonic acid; acetic acid; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1135/cccc20041768

Reference yield:

p-methoxybenzyl chloride (824-94-2) → methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (858129-92-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.33 h

1.2: dimethylformamide

2.1: 98 percent / aq. AcOH / CH₂Cl₂

3.1: 63 percent / imidazole / dimethylformamide / 20 °C

4.1: 75 percent / CuBr₂; 4 Angstroem molecular sieves / CH₂Cl₂

5.1: 49 percent / Bu₄NBr; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide

With 1H-imidazole; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; acetic acid; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1135/cccc20041768

upstream raw materials:

methyl 4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl bromide

methyl 1-thio-β-L-fucopyranoside

tert-butyldimethylsilyl chloride