(2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid

Base Information

Chemical Name:(2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid
CAS No.:130625-79-5
Molecular Formula:C₃₇H₆₀O₃Si
Molecular Weight:580.967
Hs Code.:

Synonyms:(2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid

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Chemical Property of (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid

Chemical Property:

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Technology Process of (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid

There total 30 articles about (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic 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: 62.0%

: (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanal

: 130625-79-5
(2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid

Guidance literature:: With jones' reagent; In acetone; at 0 ℃; for 0.75h;
DOI:10.1039/a804275f

Reference yield:

: 26186-02-7
tridec-1-yne

: 130625-79-5
(2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid

Guidance literature:: Multi-step reaction with 14 steps

1: 86 percent / BuLi / tetrahydrofuran / 18 h / Heating

2: 1.) dicyclohexylborane, 2.) AcOH / 1.) THF, r.t., 2 h, 2.) THF, r.t., 1 h

3: Br₂ / CH₂Cl₂ / 0.17 h / -78 °C

4: NaOMe / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 2 h

6: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature

7: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h

8: LiAlH₄ / diethyl ether / 3 h / 0 °C

9: imidazole / dimethylformamide / 1 h / Ambient temperature

10: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) reflux, 24 h

11: 91 percent / TfOH / cyclohexane; CH₂Cl₂ / 0.5 h / Ambient temperature

12: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

13: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature

14: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; jones' reagent; trifluorormethanesulfonic acid; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; dihydrogen peroxide; bromine; sodium methylate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a804275f

Reference yield:

: 130625-73-9
(Dimethyl-phenyl-silanyl)-propynoic acid

: 130625-79-5
(2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid

Guidance literature:: Multi-step reaction with 13 steps

1: 64 percent / H₂, quinoline / 10percent Pd/BaSO₄ / methanol / 3 h

2: (COCl)2, DMF / CH₂Cl₂ / 1 h / Ambient temperature

3: n-BuLi / tetrahydrofuran; hexane / 1.) -20 deg C, 20 min, 2.) r.t., 30 min

5: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature

6: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h

7: LiAlH₄ / diethyl ether / 3 h / 0 °C

8: imidazole / dimethylformamide / 1 h / Ambient temperature

9: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) reflux, 24 h

10: 91 percent / TfOH / cyclohexane; CH₂Cl₂ / 0.5 h / Ambient temperature

11: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

12: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature

13: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C

With 1H-imidazole; quinoline; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; jones' reagent; oxalyl dichloride; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; N,N-dimethyl-formamide; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a804275f