3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride

Base Information

• Chemical Name: 3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride
• CAS No.: 108194-66-7
• Molecular Formula: C₂₅H₃₅ClO₁₀
• Molecular Weight: 531

Synonyms:3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride

Chemical Property of 3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride

There total 13 articles about 3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride 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: 93.0%

3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-L-fucose → 3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride (108194-66-7)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1016/0008-6215(86)80011-8

Reference yield:

allyl 2-O-methyl-α-L-fucopyranoside (108182-36-1) → 3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride (108194-66-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) reflux, 2 h, benzene, 2.) 100 deg C

2: 1.) tetraethylammonium bromide, molecular sieves 4 Angstroem / 1.) dichloromethane, 2 h, r.t. 2.) DMF, 5 d, r.t.

3: 1 M sodium methoxide / methanol; CH₂Cl₂ / Ambient temperature

4: 92 percent / pyridine

5: 1.) tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane 2.) mercuric oxide, mercuric chloride / 1.) ethanol, toluene, water, 6 h, reflux, 2.) acetone, water, 30 min, r.t.

6: 93 percent / oxalyl chloride, N,N-dimethylformamide / CH₂Cl₂

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; oxalyl dichloride; 4 A molecular sieve; tetraethylammonium bromide; tetrabutylammomium bromide; sodium methylate; di(n-butyl)tin oxide; N,N-dimethyl-formamide; mercury dichloride; mercury(II) oxide; In methanol; dichloromethane;

DOI:10.1016/0008-6215(86)80011-8

Reference yield:

Allyl 3,4-O-isopropylidene-2-O-methyl-α-L-fucopyranoside (108182-35-0) → 3-O-benzyl-4-O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-fucopyranosyl chloride (108194-66-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / water / acetic acid / 0.25 h / 90 °C

2: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) reflux, 2 h, benzene, 2.) 100 deg C

3: 1.) tetraethylammonium bromide, molecular sieves 4 Angstroem / 1.) dichloromethane, 2 h, r.t. 2.) DMF, 5 d, r.t.

4: 1 M sodium methoxide / methanol; CH₂Cl₂ / Ambient temperature

5: 92 percent / pyridine

6: 1.) tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane 2.) mercuric oxide, mercuric chloride / 1.) ethanol, toluene, water, 6 h, reflux, 2.) acetone, water, 30 min, r.t.

7: 93 percent / oxalyl chloride, N,N-dimethylformamide / CH₂Cl₂

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; oxalyl dichloride; 4 A molecular sieve; tetraethylammonium bromide; tetrabutylammomium bromide; water; sodium methylate; di(n-butyl)tin oxide; N,N-dimethyl-formamide; mercury dichloride; mercury(II) oxide; In methanol; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(86)80011-8

upstream raw materials:

2-O-methyl-β-L-fucose

benzyl bromide

Allyl 3,4-O-isopropylidene-2-O-methyl-α-L-fucopyranoside

allyl 3-O-benzyl-2-O-methyl-α-L-fucopyranoside

Downstream raw materials:

benzyl O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(3-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-(1->3)-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside

benzyl O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(3-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-(1->3)-O-(2,4-di-O-acetyl-3-O-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside

benzyl O-(2-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(3-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside

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