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

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(4-chloro-phenyl)-5-cyano-6-oxo-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester
• CAS No.: 191659-59-3
• Molecular Formula: C₃₉H₄₂ClN₃O₁₉S
• Molecular Weight: 924.29

Synonyms:

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

Chemical Property:

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

There total 3 articles about Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(4-chloro-phenyl)-5-cyano-6-oxo-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-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: 59.0%

5-cyano-6-(4-chlorophenyl)-2-thiouracil (70638-56-1) + 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-[4-(4-chloro-phenyl)-5-cyano-6-oxo-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester (191659-59-3)

Guidance literature:

With potassium hydroxide; In water; acetone; for 4h; Ambient temperature;

DOI:10.1080/07328319708001360

Reference yield:

4-chlorobenzaldehyde (104-88-1) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(4-chloro-phenyl)-5-cyano-6-oxo-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester (191659-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / ethanol / Heating

2: CH₃COOH / H₂O

3: 59 percent / KOH / H₂O; acetone / 4 h / Ambient temperature

With potassium hydroxide; potassium carbonate; acetic acid; In ethanol; water; acetone;

DOI:10.1080/07328319708001360

Reference yield:

Potassium; 6-(4-chloro-phenyl)-5-cyano-4-oxo-1,4-dihydro-pyrimidine-2-thiolate → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(4-chloro-phenyl)-5-cyano-6-oxo-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester (191659-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₃COOH / H₂O

2: 59 percent / KOH / H₂O; acetone / 4 h / Ambient temperature

With potassium hydroxide; acetic acid; In water; acetone;

DOI:10.1080/07328319708001360

upstream raw materials:

5-cyano-6-(4-chlorophenyl)-2-thiouracil

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

4-chlorobenzaldehyde

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