Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester

Base Information

• Chemical Name: Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester
• CAS No.: 176747-31-2
• Molecular Formula: C₃₇H₅₁N₃O₈SSi₂
• Molecular Weight: 754.064

Synonyms:Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester

Chemical Property of Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester

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Technology Process of Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester

There total 5 articles about Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-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: 76.0%

thiobenzoic acid (98-91-9) + Methanesulfonic acid 2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl ester (176747-30-1) → Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester (176747-31-2)

Guidance literature:

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

DOI:10.1021/ja960091t

Reference yield:

N-[1-((2R,3R,3aR,9aR)-3-Allyloxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide → Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester (176747-31-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / N-methylmorpholine N-oxide, aq. OsO₄ / acetone / 2.5 h / Ambient temperature

2: 97 percent / aq. NaIO₄ / dioxane / 4.5 h / Ambient temperature

3: 93 percent / NaBH₄ / methanol / 90 h / Ambient temperature

4: 92 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

5: 76 percent / Et₃N / dimethylformamide / Ambient temperature

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

DOI:10.1021/ja960091t

Reference yield:

N-{1-[(2R,3R,3aR,9aR)-3-(2-Hydroxy-ethoxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide (176747-29-8) → Thiobenzoic acid S-{2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl} ester (176747-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2: 76 percent / Et₃N / dimethylformamide / Ambient temperature

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

DOI:10.1021/ja960091t

upstream raw materials:

thiobenzoic acid

Methanesulfonic acid 2-[(2R,3R,3aR,9aR)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl ester

N-{2-Oxo-1-[(2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-(2-oxo-ethoxy)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-1,2-dihydro-pyrimidin-4-yl}-benzamide

N-{1-[(2R,3R,3aR,9aR)-3-(2-Hydroxy-ethoxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

Downstream raw materials:

N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-tert-butyldisulfanyl-ethoxy)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

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

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