(S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one

Base Information

• Chemical Name: (S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one
• CAS No.: 207737-55-1
• Molecular Formula: C₃₃H₄₅NO₆S
• Molecular Weight: 583.789
• Mol file: 207737-55-1.mol

Synonyms:(S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one

Chemical Property of (S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one

There total 10 articles about (S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one 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: 86.0%

toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (207737-06-2) + (S)-6-[2-(4-(tert-butoxycarbonylamino)phenyl)ethyl]-4-hydroxy-6-isopropyl-5,6-dihydropyran-2-one (207737-54-0) → (S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (207737-55-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0968-0896(99)00215-1

Reference yield:

3-methyl-butan-2-one (563-80-4) → (S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (207737-55-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 40 percent / 1 percent NaOH / tetrahydrofuran / 6 h / Heating

2.1: H₂ / 5 percent Pd/BaSO₄ / tetrahydrofuran / 0.57 h / 20 °C / 2637.45 Torr

3.1: 95 percent / tetrahydrofuran / 96 h / 20 - 55 °C

4.1: 208 g / i-Pr₂NH; n-BuLi / tetrahydrofuran / 3 h / -78 - -40 °C

5.1: 84 g / H₂ / 20 percent Pd/C / tetrahydrofuran / 7 h / 20 °C / 2637.45 Torr

6.1: (S)-α-methylbenzylamine / ethyl acetate / Heating

6.2: 1N HCl

7.1: CDI / tetrahydrofuran / 2 h / 20 °C

7.2: tetrahydrofuran / 20 °C

8.1: 13.4 g / 0.1N NaOH / tetrahydrofuran / 20 °C

9.1: 86 percent / K₂CO₃ / dimethylformamide / 20 °C

With sodium hydroxide; n-butyllithium; (S)-1-phenyl-ethylamine; hydrogen; potassium carbonate; diisopropylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; Pd-BaSO₄; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Hydrogenation / 3.1: Acylation / 4.1: Condensation / 5.1: Hydrogenolysis / 6.1: salt formation; chiral resolution / 6.2: chiral resolution / 7.1: Substitution / 7.2: Substitution / 8.1: Cyclization / 9.1: Substitution;

DOI:10.1016/S0968-0896(99)00215-1

Reference yield:

4-nitrobenzaldehdye (555-16-8) → (S)-6-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (207737-55-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 40 percent / 1 percent NaOH / tetrahydrofuran / 6 h / Heating

2.1: H₂ / 5 percent Pd/BaSO₄ / tetrahydrofuran / 0.57 h / 20 °C / 2637.45 Torr

3.1: 95 percent / tetrahydrofuran / 96 h / 20 - 55 °C

4.1: 208 g / i-Pr₂NH; n-BuLi / tetrahydrofuran / 3 h / -78 - -40 °C

5.1: 84 g / H₂ / 20 percent Pd/C / tetrahydrofuran / 7 h / 20 °C / 2637.45 Torr

6.1: (S)-α-methylbenzylamine / ethyl acetate / Heating

6.2: 1N HCl

7.1: CDI / tetrahydrofuran / 2 h / 20 °C

7.2: tetrahydrofuran / 20 °C

8.1: 13.4 g / 0.1N NaOH / tetrahydrofuran / 20 °C

9.1: 86 percent / K₂CO₃ / dimethylformamide / 20 °C

With sodium hydroxide; n-butyllithium; (S)-1-phenyl-ethylamine; hydrogen; potassium carbonate; diisopropylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; Pd-BaSO₄; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Hydrogenation / 3.1: Acylation / 4.1: Condensation / 5.1: Hydrogenolysis / 6.1: salt formation; chiral resolution / 6.2: chiral resolution / 7.1: Substitution / 7.2: Substitution / 8.1: Cyclization / 9.1: Substitution;

DOI:10.1016/S0968-0896(99)00215-1

upstream raw materials:

toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester

(S)-6-[2-(4-(tert-butoxycarbonylamino)phenyl)ethyl]-4-hydroxy-6-isopropyl-5,6-dihydropyran-2-one

3-methyl-butan-2-one

4-nitrobenzaldehdye

Downstream raw materials:

CI-1029