1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 851345-92-1
• Molecular Formula: C₁₈H₂₂N₂O₆
• Molecular Weight: 362.382

Synonyms:1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

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Technology Process of 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

There total 3 articles about 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-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: 83.0%

4'-C-benzyloxymethylene-3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilylthymidine (851345-91-0) → 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (851345-92-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1002/chem.200401114

Reference yield:

benzyl bromide (100-39-0) → 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (851345-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 40 percent / NaI / tetrahydrofuran / 2 h / 0 °C

2.1: 83 percent / TBAF / tetrahydrofuran / 7 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1002/chem.200401114

Reference yield:

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (162052-67-7) → 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (851345-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 40 percent / NaI / tetrahydrofuran / 2 h / 0 °C

2.1: 83 percent / TBAF / tetrahydrofuran / 7 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1002/chem.200401114

upstream raw materials:

4'-C-benzyloxymethylene-3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilylthymidine

benzyl bromide

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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