(2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol

Base Information

Chemical Name:(2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol
CAS No.:237735-61-4
Molecular Formula:C₂₇H₄₈O₃Si
Molecular Weight:448.762
Hs Code.:

Synonyms:(2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol

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Chemical Property of (2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol

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Technology Process of (2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol

There total 11 articles about (2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol 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: 95.0%

: 13154-24-0
triisopropylsilyl chloride

: 169897-97-6
(2R,3R,5S)-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-1,3-diol

: 237735-61-4
(2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol

Guidance literature:: With 1H-imidazole;
DOI:10.1016/S0040-4039(99)00731-5

Reference yield:

: 10385-30-5
4-(benzyloxy)butanoic acid

: 237735-61-4
(2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: triethylamine / diethyl ether / 0 - 20 °C

2.1: 88 percent / n-butyllithium / diethyl ether; tetrahydrofuran; hexane / 1 h / -78 - 0 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / -70 °C

3.2: 73 percent / tetrahydrofuran / 18 h / -50 °C

4.1: 76 percent / LiBH₄; methanol / tetrahydrofuran / 4 h / 20 °C

5.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

6.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

6.2: tetrahydrofuran / 2 h / -78 °C

7.1: 5.9 g / formic acid / diethyl ether; H₂O / 10 h / 20 °C

8.1: Bu₂BOTf; i-Pr₂EtN / CH₂Cl₂ / 1.08 h

8.2: CH₂Cl₂ / 3 h / -78 °C

8.3: 80 percent / H₂O₂ / CH₂Cl₂; methanol

9.1: 99 percent / LiBH₄; methanol / tetrahydrofuran

10.1: 95 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 0 °C

With methanol; dmap; lithium borohydride; n-butyllithium; formic acid; di-n-butylboryl trifluoromethanesulfonate; sodium hexamethyldisilazane; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 6.1: Wittig olefination;
DOI:10.1021/jo034011x

Reference yield:

: 100-39-0
benzyl bromide

: 237735-61-4
(2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: potassium hydroxide / toluene / 72 h / Heating

1.2: 97 percent / potassium hydroxide / H₂O / 24 h / Heating

2.1: triethylamine / diethyl ether / 0 - 20 °C

3.1: 88 percent / n-butyllithium / diethyl ether; tetrahydrofuran; hexane / 1 h / -78 - 0 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / -70 °C

4.2: 73 percent / tetrahydrofuran / 18 h / -50 °C

5.1: 76 percent / LiBH₄; methanol / tetrahydrofuran / 4 h / 20 °C

6.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

7.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

7.2: tetrahydrofuran / 2 h / -78 °C

8.1: 5.9 g / formic acid / diethyl ether; H₂O / 10 h / 20 °C

9.1: Bu₂BOTf; i-Pr₂EtN / CH₂Cl₂ / 1.08 h

9.2: CH₂Cl₂ / 3 h / -78 °C

9.3: 80 percent / H₂O₂ / CH₂Cl₂; methanol

10.1: 99 percent / LiBH₄; methanol / tetrahydrofuran

11.1: 95 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 0 °C

With methanol; dmap; potassium hydroxide; lithium borohydride; n-butyllithium; formic acid; di-n-butylboryl trifluoromethanesulfonate; sodium hexamethyldisilazane; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; 7.1: Wittig olefination;
DOI:10.1021/jo034011x