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

Base Information

• Chemical Name: 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
• CAS No.: 358621-68-8
• Molecular Formula: C₆₃H₈₇NO₁₄SSi₂
• Molecular Weight: 1170.62

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 10 articles about 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 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: 85.0%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + 7,10-di(triethylsilyl)-5(20)-deoxy-5(20)-sulfanyl-10-deacetylbaccatin III (358621-67-7) → 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 (358621-68-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In toluene; at 20 ℃; for 1.5h;

DOI:10.1021/jo015539+

Reference yield:

triethylsilyl chloride (994-30-9) → 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 (358621-68-8)

Guidance literature:

Multi-step reaction with 9 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

7: 21 percent / sodium borohydride / tetrahydrofuran; ethanol / 4 h / 20 °C

8: 85 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / toluene / 1.5 h / 20 °C

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

DOI:10.1021/jo015539+

Reference yield:

13-dehydro-10-deacetylbaccatin III (92950-42-0) → 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 (358621-68-8)

Guidance literature:

Multi-step reaction with 9 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

7: 21 percent / sodium borohydride / tetrahydrofuran; ethanol / 4 h / 20 °C

8: 85 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / toluene / 1.5 h / 20 °C

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

DOI:10.1021/jo015539+

upstream raw materials:

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

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

triethylsilyl chloride

13-dehydro-10-deacetylbaccatin III

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