allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Base Information

Chemical Name:allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside
CAS No.:1616860-57-1
Molecular Formula:C₅₁H₅₆Cl₃NO₁₄
Molecular Weight:1013.36
Hs Code.:

Synonyms:allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

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Chemical Property of allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

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Technology Process of allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

There total 7 articles about allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-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: 96.0%

: 1616860-55-9
allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 123-76-2
levulinic acid

: 1616860-57-1
allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1002/adsc.201400269

Reference yield:

: 1061181-49-4
allyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 1616860-57-1
allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 15-crown-5; sodium hydroxide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 8 h / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C

3.1: 15-crown-5; sodium hydroxide / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

3.2: 20 h / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 0 - 20 °C

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 20 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 15-crown-5; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; potassium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/adsc.201400269

Reference yield:

: 1616860-54-8
allyl (2,3-di-O-benzyl-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 1616860-57-1
allyl (methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium carbonate; dicyclohexyl-carbodiimide; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/adsc.201400269