(2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone

Base Information

• Chemical Name: (2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone
• CAS No.: 101750-89-4
• Molecular Formula: C₁₈H₂₆O₃S
• Molecular Weight: 322.469
• Mol file: 101750-89-4.mol

Synonyms:(2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone

Chemical Property of (2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone

There total 8 articles about (2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone 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: 53.0%

2-ethyl-2-(3'-oxo-5'-phenylthio-amyl)-cyclopentane-1,3-dione (101750-88-3) → (2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone (101750-89-4) + (2R,3S)-(+)-2-ethyl-2-(3'-oxo-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone (101765-05-3)

Guidance literature:

With sodium hydroxide; sodium nitrate; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; D-glucose; saccharomyces cerevisiae (2.346); toween 80; potassium chloride; magnesium sulfate; iron(II) sulfate; corn starch; In ethanol; at 30 ℃; for 25h;

DOI:10.1016/S0040-4020(01)82341-3

Reference yield:

2-(2-Phenylsulfanyl-ethyl)-[1,3]dithiane (73401-98-6) → (2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone (101750-89-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium / 1.) tetrahydrofuran/hexane, -78 deg C, then to -35 deg C, 1.5 h, 2.) -70 deg C, then 10 deg C, 2 d

2: 65 percent / mercury(II) chloride, calcium carbonate / acetonitrile; H₂O / 9 h / Heating

3: 85 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

4: 75 percent / triethylamine, hydroquinone / tetrahydrofuran / 14 h / Heating

5: 13 percent / saccharomyces cerevisiae (2.346), glucose, corn starch, K₂HPO₄, NaNO₃, KH₂PO₄, MgSO₄, KCl, FeSO₄, 6 N aq. sodium hydroxide, toween 80 / ethanol / 25 h / 30 °C / pH= 6.7-7.0

With pyridine; sodium hydroxide; sodium nitrate; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; n-butyllithium; D-glucose; saccharomyces cerevisiae (2.346); toween 80; potassium chloride; magnesium sulfate; iron(II) sulfate; triethylamine; hydroquinone; calcium carbonate; mercury dichloride; corn starch; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)82341-3

Reference yield:

3-oxo-5-phenylthio-amyl mesylate (101750-87-2) → (2R,3S)-(+)-2-ethyl-2-(3'-hydroxy-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone (101750-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / triethylamine, hydroquinone / tetrahydrofuran / 14 h / Heating

2: 13 percent / saccharomyces cerevisiae (2.346), glucose, corn starch, K₂HPO₄, NaNO₃, KH₂PO₄, MgSO₄, KCl, FeSO₄, 6 N aq. sodium hydroxide, toween 80 / ethanol / 25 h / 30 °C / pH= 6.7-7.0

With sodium hydroxide; sodium nitrate; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; D-glucose; saccharomyces cerevisiae (2.346); toween 80; potassium chloride; magnesium sulfate; iron(II) sulfate; triethylamine; hydroquinone; corn starch; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4020(01)82341-3

upstream raw materials:

(2R,3S)-(+)-2-ethyl-2-(3'-oxo-5'-phenylthio-amyl)-3-hydroxy-cyclopentanone

2-ethyl-2-(3'-oxo-5'-phenylthio-amyl)-cyclopentane-1,3-dione

2-(2-Phenylsulfanyl-ethyl)-[1,3]dithiane

phenyl 3-oxo-5-hydroxy-amyl sulfide

Downstream raw materials:

(2R,3S)-2-ethyl-2-(3'-acetoxy-5'-phenylsulfinyl-amyl)-3-acetoxy-cyclopentanone