(E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone

Base Information

Chemical Name:(E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone
CAS No.:1331733-71-1
Molecular Formula:C₅₀H₅₂INO₁₄
Molecular Weight:1017.87
Hs Code.:

Synonyms:(E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone

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Chemical Property of (E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone

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Technology Process of (E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone

There total 6 articles about (E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone 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: 60.0%

: 1331733-69-7
N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-[(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)ethyn-2-yl]benzamide

: 1331733-71-1
(E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone

Guidance literature:: With iodine; sodium hydrogencarbonate; In acetonitrile; at 25 ℃; for 15h; Inert atmosphere;
DOI:10.1039/c1cc13078a

Reference yield:

: 178263-03-1
trimethyl(2,3,4-tri-O-benzyl-α-L-fucosylethyn-2-yl)silane

: 1331733-71-1
(E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 16 h / 25 °C

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 80 °C

3: iodine; sodium hydrogencarbonate / acetonitrile / 15 h / 25 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; iodine; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; 2: Sonogashira coupling;
DOI:10.1039/c1cc13078a

Reference yield:

: 151909-89-6
1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose

: 1331733-71-1
(E)-3-((2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)iodomethylene)-N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)isoindolinone

Guidance literature:: Multi-step reaction with 4 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 25 °C / Inert atmosphere; Molecular sieve

2: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 16 h / 25 °C

3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 80 °C

4: iodine; sodium hydrogencarbonate / acetonitrile / 15 h / 25 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3: Sonogashira coupling;
DOI:10.1039/c1cc13078a