(R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid

Base Information

• Chemical Name: (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid
• CAS No.: 82599-18-6
• Molecular Formula: C₄₁H₇₂ClNO₉Si₂
• Molecular Weight: 814.648

Synonyms:(R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid

Chemical Property of (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid

Chemical Property:

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Technology Process of (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid

There total 21 articles about (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid 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: 52.0%

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid ethyl ester (82599-17-5) → (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid (82599-18-6)

Guidance literature:

With potassium hydroxide; ethanol; In tetrahydrofuran; at 45 ℃; for 7h;

DOI:10.1021/ja00382a065

Reference yield:

(2-Chloro-5-iodomethyl-3-methoxy-phenyl)-methyl-carbamic acid methyl ester (82599-00-6) → (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid (82599-18-6)

Guidance literature:

Multi-step reaction with 14 steps

2: ozone / -78 °C

3: NaBH₄ / ethanol / 0.5 h / 0 °C

4: PBr₃, LiBr, collidine / diethyl ether; tetrahydrofuran

5: nitromethane

6: t-BuLi / tetrahydrofuran; dimethylformamide / -63 °C

7: 78 percent / tetrahydrofuran / -63 deg C -> room temperature

8: H₂O, AcOH / tetrahydrofuran / 48 h / -10 °C

9: 1.) NaBH₄, 2.) KOH, EtOH / 1.) MeOH, 0 deg C, 15 min, 2.) reflux, 22 h

10: 70 percent / t-BuOOH, Ti(O-i-Pr)4 / CH₂Cl₂ / 1.5 h / -20 °C

11: aldol reaction

12: tetrahydrofuran / 0.5 h / -78 °C

13: imidazole / dimethylformamide / 12 h / 35 °C

14: 52 percent / KOH, EtOH / tetrahydrofuran / 7 h / 45 °C

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; ethanol; water; tert.-butyl lithium; phosphorus tribromide; ozone; acetic acid; lithium bromide; In tetrahydrofuran; diethyl ether; nitromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00382a065

Reference yield:

[2-Chloro-3-methoxy-5-((E)-2-methyl-4-oxo-but-2-enyl)-phenyl]-methyl-carbamic acid methyl ester (67705-17-3) → (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid (82599-18-6)

Guidance literature:

Multi-step reaction with 12 steps

1: NaBH₄ / ethanol / 0.5 h / 0 °C

2: PBr₃, LiBr, collidine / diethyl ether; tetrahydrofuran

3: nitromethane

4: t-BuLi / tetrahydrofuran; dimethylformamide / -63 °C

5: 78 percent / tetrahydrofuran / -63 deg C -> room temperature

6: H₂O, AcOH / tetrahydrofuran / 48 h / -10 °C

7: 1.) NaBH₄, 2.) KOH, EtOH / 1.) MeOH, 0 deg C, 15 min, 2.) reflux, 22 h

8: 70 percent / t-BuOOH, Ti(O-i-Pr)4 / CH₂Cl₂ / 1.5 h / -20 °C

9: aldol reaction

10: tetrahydrofuran / 0.5 h / -78 °C

11: imidazole / dimethylformamide / 12 h / 35 °C

12: 52 percent / KOH, EtOH / tetrahydrofuran / 7 h / 45 °C

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; ethanol; water; tert.-butyl lithium; phosphorus tribromide; acetic acid; lithium bromide; In tetrahydrofuran; diethyl ether; nitromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00382a065

upstream raw materials:

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-{(2S,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-propionic acid ethyl ester

(2-Chloro-5-iodomethyl-3-methoxy-phenyl)-methyl-carbamic acid methyl ester

[2-Chloro-5-((E)-4-hydroxy-2-methyl-but-2-enyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

[2-Chloro-3-methoxy-5-((E)-2-methyl-4-oxo-but-2-enyl)-phenyl]-methyl-carbamic acid methyl ester

Downstream raw materials:

(+/-)-maytansinol

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