Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester
• CAS No.: 169304-16-9
• Molecular Formula: C₂₈H₂₆N₂O₉S
• Molecular Weight: 566.588

Synonyms:Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 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: 75.0%

4-Furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile + 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide (14227-90-8) → Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester (169304-16-9)

Guidance literature:

With potassium hydroxide; In acetone; Ambient temperature;

DOI:10.1080/15257779508009493

Reference yield:

4-Furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile → Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester (169304-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: (NH₄)2SO₄ / Heating

2: SnCl₄ / acetonitrile / Ambient temperature

With ammonium sulfate; tin(IV) chloride; In acetonitrile;

DOI:10.1080/15257779508009493

Reference yield:

4-Furan-2-yl-6-(4-methoxy-phenyl)-2-trimethylsilanylsulfanyl-nicotinonitrile + 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose (4258-00-8) → Acetic acid (2R,3R,4S,5S)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester (169304-16-9)

Guidance literature:

With tin(IV) chloride; In acetonitrile; Yield given; Ambient temperature;

DOI:10.1080/15257779508009493

upstream raw materials:

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide

1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose

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