5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
CAS No.:188559-40-2
Molecular Formula:C₂₈H₂₅ClN₂O₅
Molecular Weight:504.97
Hs Code.:

Synonyms:5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

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Chemical Property of 5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

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Technology Process of 5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

There total 8 articles about 5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-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: 55.0%

: 188559-37-7
2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-chloro-3H-pyrimidin-4-one

: 188559-40-2
5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: With pyridine hydrogenfluoride; In 1,4-dioxane;
DOI:10.1016/S0040-4039(96)02520-8

Reference yield:

: 134485-31-7
5,5-Dibenzyloxy-2E-penten-1-ol

: 188559-40-2
5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N, DMAP

2: K₂OsO₄*2H₂O, K₃Fe(CN)6, K₂CO₃, DHQD-PHN / H₂O; 2-methyl-propan-2-ol

3: H₂SO₄ / tetrahydrofuran / 0 °C

4: 67 percent / NaH / dimethylformamide

5: 75 percent / Rh(PPh₃)3Cl, pyridine / aq. ethanol / 5 h / Heating

6: 55 percent / pyridine*HF / dioxane

With pyridine; dmap; potassium osmate(VI); Wilkinson's catalyst; sulfuric acid; sodium hydride; potassium carbonate; pyridine hydrogenfluoride; 9-O-(9'-phenanthryl) ether of dihydroquinidine; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0040-4039(96)02520-8

Reference yield:

: 134485-39-5
(E)-5,5-Bis-benzyloxy-pent-2-enoic acid ethyl ester

: 188559-40-2
5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1: DIBAL-H / diethyl ether / -78 °C

2: Et₃N, DMAP

3: K₂OsO₄*2H₂O, K₃Fe(CN)6, K₂CO₃, DHQD-PHN / H₂O; 2-methyl-propan-2-ol

4: H₂SO₄ / tetrahydrofuran / 0 °C

5: 67 percent / NaH / dimethylformamide

6: 75 percent / Rh(PPh₃)3Cl, pyridine / aq. ethanol / 5 h / Heating

7: 55 percent / pyridine*HF / dioxane

With pyridine; dmap; potassium osmate(VI); Wilkinson's catalyst; sulfuric acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; 9-O-(9'-phenanthryl) ether of dihydroquinidine; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0040-4039(96)02520-8