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

Base Information

• Chemical Name: 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil
• CAS No.: 289906-51-0
• Molecular Formula: C₂₅H₂₅N₃O₁₀S
• Molecular Weight: 559.554

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

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

Chemical Property:

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

There total 5 articles about 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-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: 65.0%

4-phenyl-6-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidine-5-carbonitrile + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil (289906-51-0)

Guidance literature:

With tin(IV) chloride; In acetonitrile; at 23 ℃; for 16h;

DOI:10.1016/S0040-4020(00)00807-3

Reference yield: 49.0%

5-cyano-6-phenyl-2-thiouracil (70638-52-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil (289906-51-0) + 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)-5-cyano-6-phenyl-pyrimidin-4(1H)-one

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: 35.0%

2-mercapto-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile; compound with piperidine + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil (289906-51-0) + 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)-5-cyano-6-phenyl-pyrimidin-4(1H)-one

Guidance literature:

In water; acetone; at 23 ℃; for 6h;

DOI:10.1016/S0040-4020(00)00807-3

upstream raw materials:

5-cyano-6-phenyl-2-thiouracil

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

Downstream raw materials:

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

C₂₃H₂₁N₃O₈S

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