O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose

Base Information

• Chemical Name: O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose
• CAS No.: 1379653-34-5
• Molecular Formula: C₅₅H₄₈Cl₃NO₁₉
• Molecular Weight: 1133.34

Synonyms:O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose

Chemical Property of O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose

There total 7 articles about O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose 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: 62.0%

4-methoxyphenyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside (1379653-32-3) + trichloroacetonitrile (545-06-2) → O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose (1379653-34-5)

Guidance literature:

4-methoxyphenyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside; With ammonium cerium (IV) nitrate; In water; toluene; acetonitrile; at 20 ℃; for 0.5h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.carres.2012.03.039

Reference yield:

6-(methoxycarbonyl)-5-(4-oxopentanoyloxy)-2-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate → O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose (1379653-34-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.67 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 3 h / 0 °C

3.1: pyridine / dichloromethane / 2 h / 0 °C

4.1: ammonium cerium (IV) nitrate / water; toluene; acetonitrile / 0.5 h / 20 °C

4.2: 0.5 h / 20 °C

With pyridine; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/j.carres.2012.03.039

Reference yield:

4-methoxyphenyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2-O-benzoyl-β-D-galactopyranoside (1379653-31-2) → O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-1-O-trichloroacetimidoyl-β-D-galactopyranose (1379653-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / dichloromethane / 2 h / 0 °C

2.1: ammonium cerium (IV) nitrate / water; toluene; acetonitrile / 0.5 h / 20 °C

2.2: 0.5 h / 20 °C

With pyridine; ammonium cerium (IV) nitrate; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/j.carres.2012.03.039

upstream raw materials:

methyl (4-methoxyphenyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosid)uronate

4-methoxyphenyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2-O-benzoyl-4,6-O-di-tert-butylsilylene-β-D-galactopyranoside

4-methoxyphenyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2-O-benzoyl-β-D-galactopyranoside

4-methoxyphenyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside

Downstream raw materials:

2-benzyloxycarbonylaminoethyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-di-O-tert-butylsilylene-β-D-galactopyranoside

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