7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxo-10-deacetylbaccatin III

Base Information

• Chemical Name: 7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxo-10-deacetylbaccatin III
• CAS No.: 358621-66-6
• Molecular Formula: C₄₁H₆₂O₉SSi₂
• Molecular Weight: 787.175

Synonyms:7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxo-10-deacetylbaccatin III

Chemical Property of 7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxo-10-deacetylbaccatin III

Chemical Property:

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Technology Process of 7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxo-10-deacetylbaccatin III

There total 8 articles about 7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxo-10-deacetylbaccatin III 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: 74.0%

phenyllithium (591-51-5) + 2-debenzoyl-7,10-di(triethylsilyl)-5(20)-deoxy-5(20)-sulfanyl-13-oxo-10-deacetylbaccatin III 1,2 carbonate (358621-63-3) → 7,10-di(triethylsilyl)-5(20)-deoxy-5(20)-sulfanyl-13-oxo-10-deacetylbaccatin III (358621-66-6)

Guidance literature:

In tetrahydrofuran; hexane; at -72 ℃; for 1h;

DOI:10.1021/jo015539+

Reference yield:

triethylsilyl chloride (994-30-9) → 7,10-di(triethylsilyl)-5(20)-deoxy-5(20)-sulfanyl-13-oxo-10-deacetylbaccatin III (358621-66-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 69 percent / imidazole / dimethylformamide / 15 h / 20 °C

2: 59 percent / Red-Al / toluene; tetrahydrofuran / 0.33 h / 0 °C

3: 93 percent / pyridine / CH₂Cl₂ / 0.33 h / -18 °C

4: 63 percent / tetraethylammonium bromide; BF₃*Et₂O / CH₂Cl₂ / 0.75 h / 20 °C

5: 72 percent / tributylphosphine; diethyl azodicarboxylate / dimethylformamide / 44 h / 20 °C

6: 74 percent / tetrahydrofuran; hexane / 1 h / -72 °C

With pyridine; 1H-imidazole; tributylphosphine; boron trifluoride diethyl etherate; tetraethylammonium bromide; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo015539+

Reference yield:

13-dehydro-10-deacetylbaccatin III (92950-42-0) → 7,10-di(triethylsilyl)-5(20)-deoxy-5(20)-sulfanyl-13-oxo-10-deacetylbaccatin III (358621-66-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 69 percent / imidazole / dimethylformamide / 15 h / 20 °C

2: 59 percent / Red-Al / toluene; tetrahydrofuran / 0.33 h / 0 °C

3: 93 percent / pyridine / CH₂Cl₂ / 0.33 h / -18 °C

4: 63 percent / tetraethylammonium bromide; BF₃*Et₂O / CH₂Cl₂ / 0.75 h / 20 °C

5: 72 percent / tributylphosphine; diethyl azodicarboxylate / dimethylformamide / 44 h / 20 °C

6: 74 percent / tetrahydrofuran; hexane / 1 h / -72 °C

With pyridine; 1H-imidazole; tributylphosphine; boron trifluoride diethyl etherate; tetraethylammonium bromide; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo015539+

upstream raw materials:

phenyllithium

2-debenzoyl-7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxo-10-deacetylbaccatin III 1,2 carbonate

triethylsilyl chloride

13-dehydro-10-deacetylbaccatin III

Downstream raw materials:

5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7,10-di(triethylsilyl)-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]-10-deacetylbaccatin III

7,10-di(triethylsilyl)-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-10-deacetylbaccatin III

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