4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

Base Information

• Chemical Name: 4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside
• CAS No.: 677767-11-2
• Molecular Formula: C₅₅H₅₈O₂₀
• Molecular Weight: 1039.05
• Mol file: 677767-11-2.mol

Synonyms:4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

Chemical Property of 4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

There total 6 articles about 4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 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: 55.0%

4-methoxyphenyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (671194-40-4) + 2-O-benzoyl-3,4,6-tri-O-levulinoyl-1-O-trichloroacetoimidoyl-α-D-galactopyranose (677767-09-8) → 4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (677767-11-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; toluene; at 20 ℃; for 0.5h;

DOI:10.1039/b314244b

Reference yield:

levulinic acid (123-76-2) → 4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (677767-11-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 5.48 g / DMAP; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h

2: 90 percent / aq. cerium(IV) ammonium nitrate / toluene; acetonitrile / 0.25 h / 20 °C

3: 1.31 g / DBU / CH₂Cl₂ / 0.5 h / 20 °C

4: 55 percent / 4 Angstroem molecular sieves; Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / 20 °C

With dmap; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In dichloromethane; toluene; acetonitrile;

DOI:10.1039/b314244b

Reference yield:

4-methoxyphenyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (671194-40-4) → 4-methoxyphenyl O-(2-O-benzoyl-3,4,6-tri-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (677767-11-2)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. CF₃COOH / 0.25 h / 20 °C

2: 5.48 g / DMAP; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h

3: 90 percent / aq. cerium(IV) ammonium nitrate / toluene; acetonitrile / 0.25 h / 20 °C

4: 1.31 g / DBU / CH₂Cl₂ / 0.5 h / 20 °C

5: 55 percent / 4 Angstroem molecular sieves; Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / 20 °C

With dmap; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; toluene; acetonitrile;

DOI:10.1039/b314244b

upstream raw materials:

4-methoxyphenyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

2-O-benzoyl-3,4,6-tri-O-levulinoyl-1-O-trichloroacetoimidoyl-α-D-galactopyranose

levulinic acid

Benzoic acid (2S,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

4-methoxyphenyl O-(2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

4-methoxyphenyl O-(2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

4-methoxyphenyl O-(2-O-benzoyl-4,6-O-di-tert-butylsilylene-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside