(S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

Base Information

Chemical Name:(S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid
CAS No.:149056-83-7
Molecular Formula:C₁₆H₂₂O₃
Molecular Weight:262.349
Hs Code.:

Synonyms:(S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

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Chemical Property of (S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

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Technology Process of (S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

There total 19 articles about (S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic 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:

: 72748-99-3,187035-29-6
(R)-1-Amino-2-(methoxymethyl)pyrrolidine

: 149056-85-9
(S)-2-[4-((1R)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

: 149056-83-7
(S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / cyclohexane / Reflux

2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C

2.2: 2.5 h / -100 - -78 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 10 h / 20 °C

5.1: Candida parapsilosis NBRC 1396 / ethanol / 30 °C / Enzymatic reaction

With dipyridinium dichromate; tetrabutyl ammonium fluoride; tert.-butyl lithium; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; cyclohexane; N,N-dimethyl-formamide; pentane;
DOI:10.1016/j.tetasy.2011.06.019

Reference yield:

: 1333080-47-9
C₁₆H₂₀O₃

: 149056-85-9
(S)-2-[4-((1R)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

: 149056-83-7
(S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

Guidance literature:: With Geotrichum candidum NBRC 4597; In ethanol; at 30 ℃; optical yield given as %de; stereoselective reaction; Enzymatic reaction;
DOI:10.1016/j.tetasy.2011.06.019

Reference yield:

: 1044064-76-7
1-[4-((4-methoxybenzyloxy)methyl)phenyl]ethanone

: 149056-85-9
(S)-2-[4-((1R)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

: 149056-83-7
(S)-2-[4-((1R,2S)-2-hydroxycyclohexylmethyl)phenyl]propionic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: potassium tert-butylate / diethyl ether / 1 h / Reflux

1.2: 20 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 4.25 h / 0 - 20 °C / Inert atmosphere

2.2: 1 h / 0 °C

3.1: Burkholderia cepacia lipase-PS / di-isopropyl ether / 12 h / 20 °C / Molecular sieve; Enzymatic reaction

4.1: methanol; potassium carbonate

5.1: 1H-imidazole; dmap / dichloromethane / 6 h / 0 - 20 °C

6.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C

7.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 1 h / 0 °C

8.1: lithium diisopropyl amide / tetrahydrofuran / 2.5 h / -78 °C

8.2: 1 h / -78 °C

8.3: 0.5 h

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

10.1: dipyridinium dichromate / N,N-dimethyl-formamide / 10 h / 20 °C

11.1: Candida parapsilosis NBRC 1396 / ethanol / 30 °C / Enzymatic reaction

With 1H-imidazole; methanol; dmap; N-Bromosuccinimide; dipyridinium dichromate; dimethylsulfide borane complex; Burkholderia cepacia lipase-PS; potassium tert-butylate; tetrabutyl ammonium fluoride; water; potassium carbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; di-isopropyl ether; N,N-dimethyl-formamide; 1.1: Wittig reaction / 1.2: Wittig reaction;
DOI:10.1016/j.tetasy.2011.06.019