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

Base Information

• Chemical Name: 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
• CAS No.: 187245-17-6
• Molecular Formula: C₃₀H₄₈N₂O₆SSi₂
• Molecular Weight: 620.958

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 8 articles about 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 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: 86.0%

thiobenzoic acid (98-91-9) + 3',5'-bis-O-(tert-butyldimethylsilyl)-C5-(2-methanesulfonylethyl)-2'-deoxyuridine → 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 (187245-17-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ja963285h

Reference yield:

C5-chloromercuri-2'-deoxyuridine (65505-76-2) → 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 (187245-17-6)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; palladium dichloride; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja963285h

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 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 (187245-17-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / imidazole / dimethylformamide / 3 h

2: 82 percent / N-methylmorpholine N-oxide, OsO₄ / H₂O; acetone / 3 h / in the dark

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

4: 68 percent / NaBH₄ / methanol / 3 h

5: 88 percent / Py / CH₂Cl₂ / 0 - 20 °C

6: 86 percent / Et₃N / dimethylformamide

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja963285h

upstream raw materials:

thiobenzoic acid

C⁵-chloromercuri-2'-deoxyuridine

tert-butyldimethylsilyl chloride

3',5'-bis-O-(tert-butyldimethylsilyl)-C⁵-(allyl)-2'-deoxyuridine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-C⁵-(ethyl)-2'-deoxyuridine tert-butyl disulfide

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

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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