9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-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)-6-methyl-tetradecanoic acid tert-butyl ester
CAS No.:259738-80-2
Molecular Formula:C₄₂H₇₅NO₈Si
Molecular Weight:750.145
Hs Code.:

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

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

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

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

There total 31 articles about 9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-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: 76.0%

: 259738-79-9
(6R,9R)-9-Hydroxy-6-methyl-tetradecanoic acid tert-butyl ester

: 259738-72-2
2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid

: 259738-80-2
9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-6-methyl-tetradecanoic acid tert-butyl ester

Guidance literature:: 2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

(6R,9R)-9-Hydroxy-6-methyl-tetradecanoic acid tert-butyl ester; With dmap; In toluene; at 20 ℃; for 6h;
DOI:10.1055/s-0037-1610694

Reference yield:

: 1117-61-9
(3R)-citronellol

: 259738-80-2
9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-6-methyl-tetradecanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 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: sec-BuLi / tetrahydrofuran / 4 h / -78 - 20 °C

11: H₂ / Pd(OH)2 / methanol / 15 h / 20 °C

12: DMAP / toluene / 3 h / 20 °C

With 2,6-dimethylpyridine; dichloro-acetic acid; dmap; [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; hydrogen; sec.-butyllithium; 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: Wittig olefination / 11: Catalytic hydrogenation / 12: Esterification;
DOI:10.7164/antibiotics.52.1146

Reference yield:

: 180908-43-4
(4R)-4-methyl-6-hydroxyhexan-1-al

: 259738-80-2
9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-6-methyl-tetradecanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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: sec-BuLi / tetrahydrofuran / 4 h / -78 - 20 °C

10: H₂ / Pd(OH)2 / methanol / 15 h / 20 °C

11: DMAP / toluene / 3 h / 20 °C

With 2,6-dimethylpyridine; dichloro-acetic acid; dmap; [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; hydrogen; sec.-butyllithium; 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: Wittig olefination / 10: Catalytic hydrogenation / 11: Esterification;
DOI:10.7164/antibiotics.52.1146