4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Base Information

Chemical Name:4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran
CAS No.:259137-62-7
Molecular Formula:C₂₅H₃₀N₂O₅Si
Molecular Weight:466.609
Hs Code.:

Synonyms:4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

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Chemical Property of 4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

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Technology Process of 4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

There total 8 articles about 4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran 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: 54.0%

: 259137-60-5
4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

: 259137-62-7
4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

: 4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Guidance literature:: With sulfuric acid; In 1,4-dioxane; at 100 ℃; for 2.5h;
DOI:10.1080/07328319908044614

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 259137-62-7
4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / imidazole / dimethylformamide / 18 h / 70 °C

2: 93 percent / H₂ / Pd/C / ethyl acetate; ethanol / 6 h / 1292.87 Torr

3: 93 percent / toluene / 2.5 h / 0 - 20 °C

4: 54 percent / aq. H₂SO₄ / dioxane / 2.5 h / 100 °C

With 1H-imidazole; sulfuric acid; hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Reduction / 3: Addition / 4: Cyclization;
DOI:10.1080/07328319908044614

Reference yield:

: 491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9
1,4-anhydro-D-ribitol

: 259137-62-7
4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

4: 87 percent / imidazole / dimethylformamide / 18 h / 70 °C

5: 93 percent / H₂ / Pd/C / ethyl acetate; ethanol / 6 h / 1292.87 Torr

6: 93 percent / toluene / 2.5 h / 0 - 20 °C

7: 54 percent / aq. H₂SO₄ / dioxane / 2.5 h / 100 °C

With pyridine; 1H-imidazole; thionyl chloride; sodium azide; sulfuric acid; hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Cyclization / 3: Ring cleavage / 4: Substitution / 5: Reduction / 6: Addition / 7: Cyclization;
DOI:10.1080/07328319908044614