(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

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 ethyl ester
• CAS No.: 82599-17-5
• Molecular Formula: C₄₃H₇₆ClNO₉Si₂
• Molecular Weight: 842.702

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 ethyl ester

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 ethyl ester

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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 ethyl ester

There total 20 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 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-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}-3-hydroxy-propionic acid ethyl ester (82599-16-4) → (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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 35 ℃; for 12h;

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 ethyl ester (82599-17-5)

Guidance literature:

Multi-step reaction with 13 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

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 ethyl ester (82599-17-5)

Guidance literature:

Multi-step reaction with 11 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

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:

tert-butyldimethylsilyl chloride

(S)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-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}-3-hydroxy-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

Downstream 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

(+/-)-maytansinol

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