1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one

Base Information

• Chemical Name: 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one
• CAS No.: 1338917-06-8
• Molecular Formula: C₂₅H₂₆N₄O₁₀
• Molecular Weight: 542.502
• Mol file: 1338917-06-8.mol

Synonyms:1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one

Chemical Property of 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one

There total 4 articles about 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one 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: 78.0%

2,4-dioxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (37465-59-1) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one (1338917-06-8)

Guidance literature:

2,4-dioxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 70 - 80 ℃; for 1h;

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester; In N,N-dimethyl-formamide; mineral oil; at 90 ℃;

DOI:10.1002/jhet.686

Reference yield:

D-glucosamine hydrochloride (14131-62-5) → 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one (1338917-06-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium / methanol / 25 °C

1.2: 0 - 20 °C

2.1: acetyl chloride / 48 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 70 - 80 °C

3.2: 90 °C

With sodium; sodium hydride; acetyl chloride; In methanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/jhet.686

Reference yield:

benzaldehyde (100-52-7) → 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one (1338917-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / ethanol / 20 h / Reflux

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 70 - 80 °C

2.2: 90 °C

With sodium hydride; potassium carbonate; In ethanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/jhet.686

upstream raw materials:

D-glucosamine hydrochloride

benzaldehyde

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose

2,4-dioxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile

Downstream raw materials:

1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenyl-pyrimidin-4(1H)-one