4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile

Base Information

• Chemical Name: 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile
• CAS No.: 1313588-82-7
• Molecular Formula: C₂₇H₂₃ClN₂O₈S
• Molecular Weight: 571.007

Synonyms:4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile

Chemical Property of 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile

Chemical Property:

Purity/Quality:

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Technology Process of 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile

There total 5 articles about 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile 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: 58.0%

1,2,3,5-tetra-O-acetyl-β-D-xylofuranose (23094-61-3) + 4-(4-chlorophenyl)-2-oxo-6-(thien-2-yl)-1,2-dihydropyridine-3-carbonitrile (120238-95-1) → 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile (1313588-82-7)

Guidance literature:

With silica gel; for 0.0833333h; Microwave irradiation;

DOI:10.1016/j.ejmech.2011.04.019

Reference yield: 52.0%

2,3,5-tri-O-acetyl-α-D-xylofuranosyl bromide (55057-30-2) + 4-(4-chlorophenyl)-2-oxo-6-(thien-2-yl)-1,2-dihydropyridine-3-carbonitrile (120238-95-1) → 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile (1313588-82-7)

Guidance literature:

4-(4-chlorophenyl)-2-oxo-6-(thien-2-yl)-1,2-dihydropyridine-3-carbonitrile; With potassium carbonate; In N,N-dimethyl-formamide; acetone; for 1h;

2,3,5-tri-O-acetyl-α-D-xylofuranosyl bromide; In N,N-dimethyl-formamide; acetone; Reflux;

DOI:10.1016/j.ejmech.2011.04.019

Reference yield:

2-Acetylthiophene (88-15-3,97511-16-5) → 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile (1313588-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide

2.1: ammonium acetate / ethanol / 10 h / Reflux

3.1: potassium carbonate / N,N-dimethyl-formamide; acetone / 1 h

3.2: Reflux

With ammonium acetate; potassium carbonate; sodium hydroxide; In ethanol; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.ejmech.2011.04.019

upstream raw materials:

2-Acetylthiophene

2,3,5-tri-O-acetyl-α-D-xylofuranosyl bromide

4-(4-chlorophenyl)-2-oxo-6-(thien-2-yl)-1,2-dihydropyridine-3-carbonitrile

1,2,3,5-tetra-O-acetyl-β-D-xylofuranose

Downstream raw materials:

4-(4-chlorophenyl)-2-(β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile

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