Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester

Base Information

Chemical Name:Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester
CAS No.:187245-20-1
Molecular Formula:C₁₈H₂₀N₂O₆S
Molecular Weight:392.433
Hs Code.:

Synonyms:Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester

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Chemical Property of Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester

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Technology Process of Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester

There total 8 articles about Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester 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: 90.0%

: 187245-17-6
Thiobenzoic acid S-(2-{1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-ethyl) ester

: 187245-20-1
Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h;
DOI:10.1021/ja963285h

Reference yield:

: 65505-76-2
C⁵-chloromercuri-2'-deoxyuridine

: 187245-20-1
Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester

Guidance literature:: Multi-step reaction with 8 steps

1: 78 percent / LiCl₂, PdCl₂ / methanol / 20 h

2: 78 percent / imidazole / dimethylformamide / 3 h

3: 82 percent / N-methylmorpholine N-oxide, OsO₄ / H₂O; acetone / 3 h / in the dark

4: 97 percent / NaIO₄ / dioxane; H₂O / 3 h

5: 68 percent / NaBH₄ / methanol / 3 h

6: 88 percent / Py / CH₂Cl₂ / 0 - 20 °C

7: 86 percent / Et₃N / dimethylformamide

8: 90 percent / n-Bu₄NF*H₂O / tetrahydrofuran / 3 h

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja963285h

Reference yield:

: 151894-33-6
3',5'-bis-O-(tert-butyldimethylsilyl)-C⁵-(allyl)-2'-deoxyuridine

: 187245-20-1
Thiobenzoic acid S-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-ethyl} ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / N-methylmorpholine N-oxide, OsO₄ / H₂O; acetone / 3 h / in the dark

2: 97 percent / NaIO₄ / dioxane; H₂O / 3 h

3: 68 percent / NaBH₄ / methanol / 3 h

4: 88 percent / Py / CH₂Cl₂ / 0 - 20 °C

5: 86 percent / Et₃N / dimethylformamide

6: 90 percent / n-Bu₄NF*H₂O / tetrahydrofuran / 3 h

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja963285h