5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil

Base Information

• Chemical Name: 5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil
• CAS No.: 1202395-85-4
• Molecular Formula: C₂₆H₂₇N₃O₁₁S
• Molecular Weight: 589.58

Synonyms:5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil

Chemical Property of 5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil

Chemical Property:

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Technology Process of 5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil

There total 2 articles about 5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil 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: 50.0%

5-cyano-4-oxo-6-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine (70638-54-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil (1202395-85-4) + 5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)-2-pyrimidin-4(1H)-one (1202395-88-7)

Guidance literature:

With potassium hydroxide; triethylamine; In water; N,N-dimethyl-formamide; acetone; at 20 ℃; for 24h;

DOI:10.1016/j.carres.2009.09.006

Reference yield:

C15H17N3O2SSi + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil (1202395-85-4)

Guidance literature:

With tin(IV) chloride; In acetonitrile; at 5 - 20 ℃;

DOI:10.1016/j.carres.2009.09.006

Reference yield: 66.0%

5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil (1202395-85-4) + methyl iodide (74-88-4) → 5-cyano-6-p-methoxyphenyl-3-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil (1202395-90-1)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.carres.2009.09.006

upstream raw materials:

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

5-cyano-4-oxo-6-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine

Downstream raw materials:

2,2'-anhydro-2-mercapto-6-p-methoxyphenyl-1-(3,4,6-tri-O-acetyl-β-D-mannopyranosyl)pyrimidin-5(2H)-one

C₂₄H₂₃N₃O₉S

5-cyano-6-p-methoxyphenyl-3-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil

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