(+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate

Base Information

• Chemical Name: (+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate
• CAS No.: 213319-90-5
• Molecular Formula: C₇H₁₄O₂S
• Molecular Weight: 162.253
• Mol file: 213319-90-5.mol

Synonyms:(+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate

Chemical Property of (+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate

There total 1 articles about (+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate 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: 99.0%

(-)-(4S,5R,2'S,3'R)-3-(3-hydroxy-2-methylbutanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one (161755-20-0) + ethanethiol (75-08-1) → (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one (16251-45-9,17097-67-5,28044-22-6,28044-23-7,39663-75-7,54418-69-8,77943-39-6,125133-96-2,149055-02-7) + (+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate (213319-90-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1021/jo9805246

Reference yield:

(+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate (213319-90-5) → methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(hydroxymethyl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate (206762-56-3)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 100 percent / imidazole / dimethylformamide / 10 h / 20 °C

2.1: 100 percent / Et₃SiH / Pd-C / acetone / 0.25 h / 0 - 20 °C

3.1: 94 percent / LiCl; DBU / acetonitrile / 1 h / 0 °C

4.1: 100 percent / DIBALH / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 98 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

6.1: 79 percent / Bu₄NF / tetrahydrofuran / 21 h / 20 - 30 °C

7.1: 88 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 0 - 20 °C

8.1: 87 percent / Ph₃P / Pd(OAc)2 / dimethylformamide / 6.5 h / 90 °C

9.1: 76 percent / LiI / dimethylformamide / 5 h / Heating

10.1: O₃ / methanol / 0.25 h / -78 °C

10.2: Me₂S / methanol / 1 h / -78 - 20 °C

11.1: 168 mg / conc. HCl / CH₂Cl₂ / 15 h / 20 °C

12.1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

13.1: LDA / tetrahydrofuran; hexane / 0.42 h / -78 - 0 °C

13.2: tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

14.1: 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

15.1: 185 mg / DMAP; pyridine / 8.25 h / 0 - 20 °C

16.1: 63.2 mg / HgO; HgCl₂ / acetonitrile; H₂O / 3 h / 62 °C

17.1: 33.4 mg / BaBH₄ / methanol / 0.5 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; triethylsilane; dmap; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium chloride; mercury dichloride; mercury(II) oxide; lithium iodide; lithium diisopropyl amide; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: silylation / 2.1: Reduction / 3.1: Masamune-Roush olefination / 4.1: Reduction / 5.1: Acylation / 6.1: desilylation / 7.1: Esterification / 8.1: Cyclization / 9.1: Decarboxylation / 10.1: ozonolysis / 10.2: Decomposition / 11.1: Isomerization / 12.1: Cyclization / 13.1: Metallation / 13.2: Addition / 14.1: Methylation / 15.1: Acylation / 16.1: dethioacetalization / 17.1: Reduction;

DOI:10.1021/jo9805246

Reference yield:

(+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate (213319-90-5) → Benzoic acid methoxycarbonyl-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (206762-62-1)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 100 percent / imidazole / dimethylformamide / 10 h / 20 °C

2.1: 100 percent / Et₃SiH / Pd-C / acetone / 0.25 h / 0 - 20 °C

3.1: 94 percent / LiCl; DBU / acetonitrile / 1 h / 0 °C

4.1: 100 percent / DIBALH / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 98 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

6.1: 79 percent / Bu₄NF / tetrahydrofuran / 21 h / 20 - 30 °C

7.1: 88 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 0 - 20 °C

8.1: 87 percent / Ph₃P / Pd(OAc)2 / dimethylformamide / 6.5 h / 90 °C

9.1: 76 percent / LiI / dimethylformamide / 5 h / Heating

10.1: O₃ / methanol / 0.25 h / -78 °C

10.2: Me₂S / methanol / 1 h / -78 - 20 °C

11.1: 168 mg / conc. HCl / CH₂Cl₂ / 15 h / 20 °C

12.1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

13.1: LDA / tetrahydrofuran; hexane / 0.42 h / -78 - 0 °C

13.2: tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

14.1: 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

15.1: 185 mg / DMAP; pyridine / 8.25 h / 0 - 20 °C

16.1: 63.2 mg / HgO; HgCl₂ / acetonitrile; H₂O / 3 h / 62 °C

17.1: 33.4 mg / BaBH₄ / methanol / 0.5 h / 0 °C

18.1: 229 mg / Bu₃P / tetrahydrofuran / 8.2 h / 0 - 20 °C

19.1: 26.9 mg / H₂O₂ / tetrahydrofuran; H₂O / 1.2 h / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; triethylsilane; dmap; tributylphosphine; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium chloride; mercury dichloride; mercury(II) oxide; lithium iodide; lithium diisopropyl amide; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: silylation / 2.1: Reduction / 3.1: Masamune-Roush olefination / 4.1: Reduction / 5.1: Acylation / 6.1: desilylation / 7.1: Esterification / 8.1: Cyclization / 9.1: Decarboxylation / 10.1: ozonolysis / 10.2: Decomposition / 11.1: Isomerization / 12.1: Cyclization / 13.1: Metallation / 13.2: Addition / 14.1: Methylation / 15.1: Acylation / 16.1: dethioacetalization / 17.1: Reduction / 18.1: Condensation / 19.1: Elimination;

DOI:10.1021/jo9805246

upstream raw materials:

(-)-(4S,5R,2'S,3'R)-3-(3-hydroxy-2-methylbutanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one

ethanethiol

Downstream raw materials:

methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(hydroxymethyl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate

Benzoic acid methoxycarbonyl-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid ((2R,4R,5R,6R)-4-formyl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester

methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate

Refernces