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

Base Information

• Chemical Name: benzyl O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside
• CAS No.: 108182-57-6
• Molecular Formula: C₄₉H₆₈O₁₇
• Molecular Weight: 929.069
• Mol file: 108182-57-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about benzyl O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside 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: 92.0%

benzyl O-(4-O-benzoyl-2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-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 (108182-56-5) → benzyl O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside (108182-57-6)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; for 2h; Heating;

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

Reference yield:

Allyl 3,4-O-isopropylidene-2-O-methyl-α-L-fucopyranoside (108182-35-0) → benzyl O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside (108182-57-6)

Guidance literature:

Multi-step reaction with 9 steps

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

2: 1.) p-toluenesulfonic acid, 2.) aqueous acetic acid / 1.) acetonitrile, 2 h, r.t.; 2.) 10 min, r.t.

3: 82 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / Ambient temperature

4: 93 percent / 1 M sodium methoxide / methanol / 1 h / Heating

5: 45 percent / mercuric cyanide / benzene; nitromethane / 16 h

6: 1.) tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane, 2.) mercuric oxide, mercuric chloride / 1.) ethanol, toluene, water, 7 h, reflux, 2.) acetone, water, 30 min, r.t.

7: 95 percent / oxalyl chloride, N,N-dimethylformamide / CH₂Cl₂

8: 78 percent / silver triflate, 2,4,6-trimethylpyridine, molecular sieve 4 Angstroem / 1.) toluene, 1 h, -20 deg C, 2.) 1 h, r.t.

9: 92 percent / 1 M sodium methoxyde / methanol; CH₂Cl₂ / 2 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 2,4,6-trimethyl-pyridine; Wilkinson's catalyst; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; water; sodium methylate; silver trifluoromethanesulfonate; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; mercury dichloride; mercury(II) oxide; In methanol; nitromethane; dichloromethane; acetic acid; benzene;

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

Reference yield:

allyl 2-O-methyl-α-L-fucopyranoside (108182-36-1) → benzyl O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside (108182-57-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) p-toluenesulfonic acid, 2.) aqueous acetic acid / 1.) acetonitrile, 2 h, r.t.; 2.) 10 min, r.t.

2: 82 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / Ambient temperature

3: 93 percent / 1 M sodium methoxide / methanol / 1 h / Heating

4: 45 percent / mercuric cyanide / benzene; nitromethane / 16 h

5: 1.) tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane, 2.) mercuric oxide, mercuric chloride / 1.) ethanol, toluene, water, 7 h, reflux, 2.) acetone, water, 30 min, r.t.

6: 95 percent / oxalyl chloride, N,N-dimethylformamide / CH₂Cl₂

7: 78 percent / silver triflate, 2,4,6-trimethylpyridine, molecular sieve 4 Angstroem / 1.) toluene, 1 h, -20 deg C, 2.) 1 h, r.t.

8: 92 percent / 1 M sodium methoxyde / methanol; CH₂Cl₂ / 2 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 2,4,6-trimethyl-pyridine; Wilkinson's catalyst; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; mercury dichloride; mercury(II) oxide; In methanol; nitromethane; dichloromethane; benzene;

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

upstream raw materials:

benzyl O-(4-O-benzoyl-2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-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

allyl 2,3-di-O-methyl-α-L-fucopyranoside

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

allyl 2-O-methyl-α-L-fucopyranoside

Downstream raw materials:

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