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

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-cyano-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester
• CAS No.: 255391-49-2
• Molecular Formula: C₂₆H₂₅ClN₂O₉S
• Molecular Weight: 577.012
• Mol file: 255391-49-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-cyano-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: 73.0%

6-(4-chlorophenyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile (115809-11-5) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-cyano-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester (255391-49-2)

Guidance literature:

With potassium hydroxide; In water; acetone; at 20 ℃;

DOI:10.1080/07328319908044886

Reference yield:

Sodium; (Z)-3-(4-chloro-phenyl)-3-oxo-propen-1-olate (40160-35-8) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-cyano-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester (255391-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / piperidine acetate / H₂O / 0.17 h / Heating

2: 73 percent / KOH / H₂O; acetone / 20 °C

With potassium hydroxide; piperdinium acetate; In water; acetone; 1: Cycloaddition / 2: Condensation;

DOI:10.1080/07328319908044886

Reference yield: 80.0%

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-cyano-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester (255391-49-2) → 6-(4-Chloro-phenyl)-2-thioxo-1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyridine-3-carbonitrile

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 0.5h;

DOI:10.1080/07328319908044886

upstream raw materials:

6-(4-chlorophenyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Sodium; (Z)-3-(4-chloro-phenyl)-3-oxo-propen-1-olate