4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside
• CAS No.: 158194-93-5
• Molecular Formula: C₅₉H₅₉NO₁₈
• Molecular Weight: 1070.11
• Mol file: 158194-93-5.mol

Synonyms:4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside

Chemical Property of 4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside

There total 3 articles about 4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-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: 81.0%

4-methoxyphenyl 2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside (144367-30-6) + 6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate (144367-26-0) → 4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside (158194-93-5)

Guidance literature:

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.5h;

DOI:10.1016/S0008-6215(00)90971-6

Reference yield:

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-42-0) → 4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside (158194-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / dimethylformamide / 86 h

2: 81 percent / AW-300 molecular sieves, CF₃SO₃SiMe₃ / CH₂Cl₂ / 0.5 h

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90971-6

Reference yield:

6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α/β-D-glucopyranoside → 4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-isopropylidene-2-phthalimido-β-D-glucopyranoside (158194-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / 1,8-diazabicyclo<5.4.0>undec-7ene / CH₂Cl₂

2: 81 percent / AW-300 molecular sieves, CF₃SO₃SiMe₃ / CH₂Cl₂ / 0.5 h

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1016/S0008-6215(00)90971-6

upstream raw materials:

4-methoxyphenyl 2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside

6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

4-methoxyphenyl O-(2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

4-methoxyphenyl O-(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-2-phthalimido-β-D-glucopyranoside