1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
CAS No.:190583-99-4
Molecular Formula:C₂₆H₃₂N₂O₆Si
Molecular Weight:496.635
Hs Code.:

Synonyms:1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

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Chemical Property of 1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

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Technology Process of 1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

There total 6 articles about 1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-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: 60.0%

: 190583-95-0
1,2-anhydro-3,5-di-O-benzyl-α-L-arabinofuranose

: 10457-14-4
O,O'-bis-(trimethylsilyl)uracil

: 190584-00-0
1'-(3',5'-di-O-benzyl-β-L-ribofuranosyl)uracil

: 190583-99-4
1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 8h;
DOI:10.1080/07328309708006532

Reference yield:

: 100-39-0
benzyl bromide

: 190583-99-4
1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / sodium hydride / tetrahydrofuran / 4 h / Heating

2: 90 percent / acetic acid; water / 5 h / Heating

3: 60.5 percent / K₂CO₃ / pyridine / 20 h / 0 °C

4: 95 percent / potassium tert-butoxide / tetrahydrofuran / 0.17 h / 20 °C

5: 60 percent / molecular sieves (4 A) / CH₂Cl₂ / 8 h / 20 °C

With 4 A molecular sieve; potassium tert-butylate; water; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; 1: benzylation / 2: Hydrolysis / 3: Tosylation / 4: Cyclization / 5: Addition;
DOI:10.1080/07328309708006532

Reference yield:

: 51885-64-4
1,2-O-isopropylidene-β-L-arabinofuranose

: 190583-99-4
1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / sodium hydride / tetrahydrofuran / 4 h / Heating

2: 90 percent / acetic acid; water / 5 h / Heating

3: 60.5 percent / K₂CO₃ / pyridine / 20 h / 0 °C

4: 95 percent / potassium tert-butoxide / tetrahydrofuran / 0.17 h / 20 °C

5: 60 percent / molecular sieves (4 A) / CH₂Cl₂ / 8 h / 20 °C

With 4 A molecular sieve; potassium tert-butylate; water; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; 1: benzylation / 2: Hydrolysis / 3: Tosylation / 4: Cyclization / 5: Addition;
DOI:10.1080/07328309708006532