[(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid

Base Information

• Chemical Name: [(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid
• CAS No.: 129017-76-1
• Molecular Formula: C₂₆H₄₆O₅S
• Molecular Weight: 470.714
• Mol file: 129017-76-1.mol

Synonyms:[(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid

Chemical Property of [(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid

There total 8 articles about [(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic 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: 55.0%

[(1S,2R)-2-((Z)-(S)-1-Ethoxycarbonylmethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid ethyl ester (129017-83-0) → [(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid (129017-76-1)

Guidance literature:

With potassium hydroxide; In ethanol; for 18h; Ambient temperature;

DOI:10.1016/S0040-4039(00)94325-9

Reference yield:

2-cyclohexylidene ethanol (932-89-8) → [(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid (129017-76-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / Ti(OiPr)4, L-(+)-DET, (CH₃)3COOH, 4 Angstroem sieves / CH₂Cl₂ / 2 h / -25 °C

2: 40 percent / 10percent tartaric acid / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature

3: 84 percent / Et₃N / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

4: propionic acid / o-xylene / 2 h / 135 °C

5: (n-Bu)4NF / tetrahydrofuran / 1 h / Ambient temperature

6: 77 percent / D-(-)-DET, (CH₃)3COOH, TiO(iPr)4 / CH₂Cl₂ / 20 h / -25 °C

7: 1.) DMSO, (COCl)2, Et₃N, 2.) n-BuLi / 1.) CH₂Cl₂, 2.) THF, -78 deg -> 0 deg

8: 60 percent / Et₃N / ethanol / 18 h / Ambient temperature

9: 55 percent / KOH / aq. ethanol / 18 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; TiO(iPr)4; tetrabutyl ammonium fluoride; dimethyl sulfoxide; tartaric acid; triethylamine; dmap; propionic acid; In tetrahydrofuran; ethanol; dichloromethane; o-xylene; water;

DOI:10.1016/S0040-4039(00)94325-9

Reference yield:

(S)-1-(1-Oxa-spiro[2.5]oct-2-yl)-methanol (129100-11-4) → [(1S,2R)-2-((Z)-(S)-1-Carboxymethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid (129017-76-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 40 percent / 10percent tartaric acid / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature

2: 84 percent / Et₃N / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

3: propionic acid / o-xylene / 2 h / 135 °C

4: (n-Bu)4NF / tetrahydrofuran / 1 h / Ambient temperature

5: 77 percent / D-(-)-DET, (CH₃)3COOH, TiO(iPr)4 / CH₂Cl₂ / 20 h / -25 °C

6: 1.) DMSO, (COCl)2, Et₃N, 2.) n-BuLi / 1.) CH₂Cl₂, 2.) THF, -78 deg -> 0 deg

7: 60 percent / Et₃N / ethanol / 18 h / Ambient temperature

8: 55 percent / KOH / aq. ethanol / 18 h / Ambient temperature

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; TiO(iPr)4; tetrabutyl ammonium fluoride; dimethyl sulfoxide; tartaric acid; triethylamine; dmap; propionic acid; In tetrahydrofuran; ethanol; dichloromethane; o-xylene; water;

DOI:10.1016/S0040-4039(00)94325-9

upstream raw materials:

[(1S,2R)-2-((Z)-(S)-1-Ethoxycarbonylmethylsulfanyl-hexadec-2-enyl)-2-hydroxy-cyclohexyl]-acetic acid ethyl ester

2-cyclohexylidene ethanol

{(S)-2-[2-Hydroxy-eth-(E)-ylidene]-cyclohexyl}-acetic acid ethyl ester

((2R,3R,4S)-2-Hydroxymethyl-1-oxa-spiro[2.5]oct-4-yl)-acetic acid ethyl ester