methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate

Base Information

• Chemical Name: methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate
• CAS No.: 920508-52-7
• Molecular Formula: C₃₂H₃₀O₁₀S
• Molecular Weight: 606.65

Synonyms:methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate

Chemical Property of methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate

Chemical Property:

Purity/Quality:

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Technology Process of methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate

There total 2 articles about methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate 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: 89.0%

levulinic acid (123-76-2) + methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate (725228-76-2) → methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate (920508-52-7)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/hlca.200690234

Reference yield: 86.0%

levulinic anhydride (40608-06-8) + methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate (725228-76-2) → methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate (920508-52-7)

Guidance literature:

With pyridine; In 1,4-dioxane; for 18h;

DOI:10.1021/jo070704s

Reference yield: 57.0%

methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate (920508-52-7) + trifluoromethylsulfonic anhydride (358-23-6) + trichloroacetonitrile (545-06-2) → 6-(methoxycarbonyl)-5-(4-oxopentanoyloxy)-2-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate

Guidance literature:

methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfanyl)-β-D-glucopyranosyluronate; trifluoromethylsulfonic anhydride; With N-iodo-succinimide; In dichloromethane; water; at 20 ℃; for 15h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/hlca.200690234

upstream raw materials:

levulinic acid

methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate

levulinic anhydride

Downstream raw materials:

methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfinyl)-β-D-glucopyranosyluronate

3-azidopropyl (methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(methyl (2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyl) uronate)-β-D-glucopyranosyl)-β-D-glucopyranosid) uronate

3-azidopropyl (methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(methyl (2,3-di-O-benzoyl-β-D-glucopyranosyl) uronate)-β-D-glucopyranosyl)-β-D-glucopyranosid) uronate

3-azidopropyl (methyl (2,3-di-O-benzoyl-β-D-glucopyranosid) uronate)

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