9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester

Base Information

Chemical Name:9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester
CAS No.:503818-24-4
Molecular Formula:C₃₆H₆₆O₆Si₂
Molecular Weight:651.087
Hs Code.:

Synonyms:9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester

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Chemical Property of 9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester

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Technology Process of 9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester

There total 15 articles about 9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic 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: 82.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 666739-82-8
9-benzyloxy-3-(triethylsilanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-5-oxo-nonanoic acid tert-butyl ester

: 503818-24-4
9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester

Guidance literature:: With 2,6-dimethylpyridine;
DOI:10.1002/anie.200352361

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 503818-24-4
9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / diethyl ether / 0.5 h / -78 °C

1.2: 80 percent / diethyl ether / 1 h

2.1: 74 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 80 percent / H₂; (R)-RuBINAP; HCl / methanol / 17 h / 62057.8 Torr

4.1: 51 percent / imidazole / dimethylformamide / 3 h / 0 °C

5.1: 99 percent / Zn; AcOH / tetrahydrofuran / sonication

6.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; (R)-RuBINAP; hydrogen; Dess-Martin periodane; acetic acid; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja046992g

Reference yield:

: 666739-65-7
9-benzyloxy-4,4,6,8-tetramethyl-3,5-dioxo-7-(2,2,2-trichloroethoxycarbonyloxy)nonanoic acid tert-butyl ester

: 503818-24-4
9-benzyloxy-7-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-4,4,6,8-tetramethyl-5-oxononanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2: 80 percent / H₂; (R)-RuBINAP; HCl / methanol / 17 h / 62057.8 Torr

3: 51 percent / imidazole / dimethylformamide / 3 h / 0 °C

4: 99 percent / Zn; AcOH / tetrahydrofuran / sonication

5: 82 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; (R)-RuBINAP; hydrogen; Dess-Martin periodane; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja046992g