1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione
• CAS No.: 922704-65-2
• Molecular Formula: C₃₂H₂₄N₂O₆
• Molecular Weight: 532.552

Synonyms:1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione

There total 2 articles about 1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione 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: 32.4%

5-iodouracil-2,3-di-O-benzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid (231619-85-5) + tributylstannylethynylbenzene (3757-88-8) → 1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione (922704-65-2)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 24h; Heating;

DOI:10.1016/j.bmc.2006.10.046

Reference yield:

5',6'-di-O-acetyl-2',3'-di-O-benzyl-L-ascorbic acid (231619-90-2) → 1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione (922704-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,1,1,3,3,3-hexamethyldisilazane; ammonium sulfate / Heating

1.2: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 60 °C

2.1: 32.4 percent / Pd(PPh₃)2Cl₂ / tetrahydrofuran / 24 h / Heating

With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 2.1: Stille coupling;

DOI:10.1016/j.bmc.2006.10.046

Reference yield: 36.7%

1-[2-(3,4-bis-benzyloxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione (922704-65-2) → 1-[2-(3,4-dihydroxy-5-oxo-5H-furan-2-ylidene)-ethyl]-5-phenylethynyl-1H-pyrimidine-2,4-dione

Guidance literature:

With boron trichloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2006.10.046

upstream raw materials:

5-iodouracil-2,3-di-O-benzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid

tributylstannylethynylbenzene

5',6'-di-O-acetyl-2',3'-di-O-benzyl-L-ascorbic acid

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