6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid

Base Information

Chemical Name:6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid
CAS No.:906663-07-8
Molecular Formula:C₂₅H₄₃NO₅SSi
Molecular Weight:497.772
Hs Code.:

Synonyms:6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid

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Chemical Property of 6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid

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Technology Process of 6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid

There total 10 articles about 6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic 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: 91.0%

: 906662-90-6
[2-benzylsulfanyl-1-(4-methyl-5-oxotetrahydrofuran-2-yl)ethyl]carbamic acid tert-butyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 906663-07-8
6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid

Guidance literature:: [2-benzylsulfanyl-1-(4-methyl-5-oxotetrahydrofuran-2-yl)ethyl]carbamic acid tert-butyl ester; With lithium hydroxide; In 1,2-dimethoxyethane; at 20 ℃; for 3h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

With methanol; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1021/jm060154a

Reference yield:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 906663-07-8
6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: BuLi / hexane; diethyl ether / 1 h / -78 °C

1.2: ZnBr₂ / diethyl ether; hexane / -78 - 20 °C

1.3: 5 percent / diethyl ether; hexane / 6 h / -20 - 20 °C

2.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

3.1: 96 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 3 h / 2585.74 Torr

4.1: 85 percent / NaBH₄ / methanol / 5 h / -15 - 0 °C

5.1: 95 percent / AcOH / toluene / 5 h / Heating

6.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: 70 percent / tetrahydrofuran / 0.67 h / -78 °C

7.1: 75 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 48 h / 20 °C

8.1: 66 percent / imidazole; 1,1'-(azodicarbonyl)dipiperidine; PMe₃ / CH₂Cl₂; toluene / 24 h / 20 °C

9.1: aq. LiOH / 1,2-dimethoxy-ethane / 3 h / 20 °C

9.2: imidazole / dimethylformamide / 24 h / 20 °C

9.3: 91 percent / MeOH / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane; Pd-BaSO₄; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1021/jm060154a

Reference yield:

: 906662-74-6
(4S,1'R)-4-(1-hydroxy-3-methoxycarbonylprop-2-ynyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 906663-07-8
6-benzylsulfanyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-2-methylhexanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: 96 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 3 h / 2585.74 Torr

3.1: 85 percent / NaBH₄ / methanol / 5 h / -15 - 0 °C

4.1: 95 percent / AcOH / toluene / 5 h / Heating

5.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: 70 percent / tetrahydrofuran / 0.67 h / -78 °C

6.1: 75 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 48 h / 20 °C

7.1: 66 percent / imidazole; 1,1'-(azodicarbonyl)dipiperidine; PMe₃ / CH₂Cl₂; toluene / 24 h / 20 °C

8.1: aq. LiOH / 1,2-dimethoxy-ethane / 3 h / 20 °C

8.2: imidazole / dimethylformamide / 24 h / 20 °C

8.3: 91 percent / MeOH / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; hydrogen; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane; Pd-BaSO₄; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1021/jm060154a