9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester

Base Information

• Chemical Name: 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester
• CAS No.: 259738-85-7
• Molecular Formula: C₄₈H₈₉NO₉Si₂
• Molecular Weight: 880.407
• Mol file: 259738-85-7.mol

Synonyms:

Chemical Property of 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester

There total 17 articles about 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl 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:

(3R)-citronellol (1117-61-9) → 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester (259738-85-7)

Guidance literature:

Multi-step reaction with 13 steps

1: O₃; Ph₃P / CH₂Cl₂ / 2 h / -78 °C

2: toluene / 3 h / 100 °C

3: H₂ / Pd/C / ethanol / 3 h

4: PCC; AcONa / CH₂Cl₂ / 3 h / 20 °C

5: PhLi / tetrahydrofuran / 4 h / -78 - 20 °C

6: Cl₂CHCO₂H / CH₂Cl₂ / 2 h / 0 °C

7: 72 percent / [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)] / diethyl ether / 2 h / -78 °C

8: 70 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

9: 71 percent / O₃; Ph₃P / CH₂Cl₂ / 0.25 h / -78 °C

10: 66 percent / [CpTiCl((R,R)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)] / diethyl ether / 2 h / -78 °C

11: pyridine / 1 h / 0 - 20 °C

12: H₂ / Pd(OH)2 / methanol / 1 h / 20 °C

13: DMAP / toluene / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dichloro-acetic acid; dmap; [CpTiCl((R,R)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; hydrogen; sodium acetate; ozone; phenyllithium; triphenylphosphine; pyridinium chlorochromate; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; 1: ozonolysis / 2: Wittig olefination / 3: Catalytic hydrogenation / 4: Oxidation / 5: Wittig olefination / 6: vinyl ether cleavage / 7: Alkylation / 8: silylation / 9: ozonolysis / 10: Alkylation / 11: silylation / 12: Catalytic hydrogenation / 13: Esterification;

DOI:10.7164/antibiotics.52.1146

Reference yield:

(4R)-4-methyl-6-hydroxyhexan-1-al (180908-43-4) → 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester (259738-85-7)

Guidance literature:

Multi-step reaction with 12 steps

1: toluene / 3 h / 100 °C

2: H₂ / Pd/C / ethanol / 3 h

3: PCC; AcONa / CH₂Cl₂ / 3 h / 20 °C

4: PhLi / tetrahydrofuran / 4 h / -78 - 20 °C

5: Cl₂CHCO₂H / CH₂Cl₂ / 2 h / 0 °C

6: 72 percent / [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)] / diethyl ether / 2 h / -78 °C

7: 70 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8: 71 percent / O₃; Ph₃P / CH₂Cl₂ / 0.25 h / -78 °C

9: 66 percent / [CpTiCl((R,R)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)] / diethyl ether / 2 h / -78 °C

10: pyridine / 1 h / 0 - 20 °C

11: H₂ / Pd(OH)2 / methanol / 1 h / 20 °C

12: DMAP / toluene / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dichloro-acetic acid; dmap; [CpTiCl((R,R)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; hydrogen; sodium acetate; ozone; phenyllithium; triphenylphosphine; pyridinium chlorochromate; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; 1: Wittig olefination / 2: Catalytic hydrogenation / 3: Oxidation / 4: Wittig olefination / 5: vinyl ether cleavage / 6: Alkylation / 7: silylation / 8: ozonolysis / 9: Alkylation / 10: silylation / 11: Catalytic hydrogenation / 12: Esterification;

DOI:10.7164/antibiotics.52.1146

Reference yield:

tert-butyl (6R)-8-hydroxy-6-methyloctanoate (155005-10-0) → 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester (259738-85-7)

Guidance literature:

Multi-step reaction with 10 steps

1: PCC; AcONa / CH₂Cl₂ / 3 h / 20 °C

2: PhLi / tetrahydrofuran / 4 h / -78 - 20 °C

3: Cl₂CHCO₂H / CH₂Cl₂ / 2 h / 0 °C

4: 72 percent / [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)] / diethyl ether / 2 h / -78 °C

5: 70 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6: 71 percent / O₃; Ph₃P / CH₂Cl₂ / 0.25 h / -78 °C

7: 66 percent / [CpTiCl((R,R)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)] / diethyl ether / 2 h / -78 °C

8: pyridine / 1 h / 0 - 20 °C

9: H₂ / Pd(OH)2 / methanol / 1 h / 20 °C

10: DMAP / toluene / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dichloro-acetic acid; dmap; [CpTiCl((R,R)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; hydrogen; sodium acetate; ozone; phenyllithium; triphenylphosphine; pyridinium chlorochromate; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1: Oxidation / 2: Wittig olefination / 3: vinyl ether cleavage / 4: Alkylation / 5: silylation / 6: ozonolysis / 7: Alkylation / 8: silylation / 9: Catalytic hydrogenation / 10: Esterification;

DOI:10.7164/antibiotics.52.1146

upstream raw materials:

11-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-6-methyl-tetradecanoic acid tert-butyl ester

(4R)-4-methyl-6-hydroxyhexan-1-al

(3R)-citronellol

2-(tert-butyldimethylsilyloxy)ethyl bromide