allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside

Base Information

• Chemical Name: allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside
• CAS No.: 200003-72-1
• Molecular Formula: C₅₆H₆₆O₁₅
• Molecular Weight: 979.131

Synonyms:allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside

Chemical Property of allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside

There total 10 articles about allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-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:

allyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside (200003-67-4) → allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside (200003-72-1)

Guidance literature:

With potassium carbonate; In methanol; for 1h;

DOI:10.1016/S0040-4020(97)01024-7

Reference yield:

allyl 3,4,6-tri-O-benzoyl-β-D-glucopyranoside (160412-80-6) → allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside (200003-72-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / trifluoromethane sulfonic acid / CH₂Cl₂; cyclohexane / 4 h / 20 °C

2: 91 percent / sodium methoxide / methanol / 12 h

3: 77 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 50 °C / reduced pressure

4: 76 percent / dibutyltin dichloride; 2,6-di-tert-butyl-4-methylpyridine; silver triflate / toluene / 0.25 h / 20 °C

5: 82 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 24 h / 20 °C

6: 95 percent / triethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h / 20 °C

7: 96 percent / triflic acid / diethyl ether / 0.17 h / 0 °C

8: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

9: 144 mg / potassium carbonate / methanol / 1 h

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluorormethanesulfonic acid; dibutyltin chloride; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; cyclohexane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: methanolysis / 3: Cyclization / 4: glycosylation / 5: solvolysis / 6: silylation / 7: glycosylation / 8: desilylation / 9: Deacetylation;

DOI:10.1016/S0040-4020(97)01024-7

Reference yield:

allyl 2-O-benzyl-(R)-4,6-O-benzylidene-β-D-gluco-pyranoside (161277-33-4) → allyl (6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside (200003-72-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / dibutyltin dichloride; 2,6-di-tert-butyl-4-methylpyridine; silver triflate / toluene / 0.25 h / 20 °C

2: 82 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 24 h / 20 °C

3: 95 percent / triethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h / 20 °C

4: 96 percent / triflic acid / diethyl ether / 0.17 h / 0 °C

5: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

6: 144 mg / potassium carbonate / methanol / 1 h

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluorormethanesulfonic acid; dibutyltin chloride; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; toluene; 1: glycosylation / 2: solvolysis / 3: silylation / 4: glycosylation / 5: desilylation / 6: Deacetylation;

DOI:10.1016/S0040-4020(97)01024-7

upstream raw materials:

allyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside

allyl 3,4,6-tri-O-benzoyl-β-D-glucopyranoside

allyl 2-O-benzyl-(R)-4,6-O-benzylidene-β-D-gluco-pyranoside

allyl 2-O-benzyl-β-D-glucopyranoside

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