3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid

Base Information

• Chemical Name: 3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid
• CAS No.: 575444-10-9
• Molecular Formula: C₃₃H₄₁NO₆Si
• Molecular Weight: 575.777

Synonyms:3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid

Chemical Property of 3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid

There total 15 articles about 3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-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:

3,4-dihydroxy-5-methylbenzaldehyde (82628-68-0) → 3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid (575444-10-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 82 percent / Et₃N / dimethylformamide

2: 88 percent / K₂CO₃ / acetone

3: 82 percent / TBAF / tetrahydrofuran

4: 86 percent / K₂CO₃ / acetone

5: 100 percent / LiAlH₄ / diethyl ether

6: 94 percent / CBr₄; Ph₃P / tetrahydrofuran

7: NaHDMS / tetrahydrofuran / -78 °C

8: 95 percent / hydrrogen / Pd/C / ethanol / 760 Torr

9: 82 percent / DMAP; Et₃N / CH₂Cl₂

10: 93 percent / TFA / CH₂Cl₂

11: 77 percent / NaBH₃CN / acetonitrile

12: hydrogen / PdCl₂ / ethanol; tetrahydrofuran / 4137.18 Torr

13: NaHCO₃ / dimethylformamide

With dmap; lithium aluminium tetrahydride; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; palladium dichloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0040-4039(03)01082-7

Reference yield:

vanillin (121-33-5,8014-42-4) → 3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid (575444-10-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: Me₂NH / ethanol

1.2: conc. HCl; SnCl₂

1.3: AlCl₃; pyridine / CH₂Cl₂

2.1: 82 percent / Et₃N / dimethylformamide

3.1: 88 percent / K₂CO₃ / acetone

4.1: 82 percent / TBAF / tetrahydrofuran

5.1: 86 percent / K₂CO₃ / acetone

6.1: 100 percent / LiAlH₄ / diethyl ether

7.1: 94 percent / CBr₄; Ph₃P / tetrahydrofuran

8.1: NaHDMS / tetrahydrofuran / -78 °C

9.1: 95 percent / hydrrogen / Pd/C / ethanol / 760 Torr

10.1: 82 percent / DMAP; Et₃N / CH₂Cl₂

11.1: 93 percent / TFA / CH₂Cl₂

12.1: 77 percent / NaBH₃CN / acetonitrile

13.1: hydrogen / PdCl₂ / ethanol; tetrahydrofuran / 4137.18 Torr

14.1: NaHCO₃ / dimethylformamide

With dmap; lithium aluminium tetrahydride; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; dimethyl amine; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; palladium dichloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0040-4039(03)01082-7

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid (575444-10-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / DMAP; Et₃N / CH₂Cl₂

2: 93 percent / TFA / CH₂Cl₂

3: 77 percent / NaBH₃CN / acetonitrile

4: hydrogen / PdCl₂ / ethanol; tetrahydrofuran / 4137.18 Torr

5: NaHCO₃ / dimethylformamide

With dmap; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; palladium dichloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(03)01082-7

upstream raw materials:

9-fluorenylmethyl N-succinimidyl carbonate

3,4-dihydroxy-5-methylbenzaldehyde

vanillin

tert-butyldimethylsilyl chloride

Downstream raw materials:

{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-1-chlorocarbonyl-ethyl}-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

C₅₉H₈₂N₂O₁₀Si₂

C₅₃H₆₈N₂O₁₀Si

C₅₃H₆₆N₂O₁₀Si

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