(S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide

Base Information

• Chemical Name: (S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide
• CAS No.: 115133-38-5
• Molecular Formula: C₃₁H₄₄N₂O₆Si
• Molecular Weight: 568.786
• Mol file: 115133-38-5.mol

Synonyms:

Chemical Property of (S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide

There total 8 articles about (S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide 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:

(S)-3-Amino-1,4-dimethyl-pyrrolidine-2,5-dione (67513-66-0,106499-64-3,115184-83-3) → (S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide (115133-38-5)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol / 5.5 h

2: Et₃N / CH₂Cl₂ / -45 °C

3: tetrahydrofuran / 8 h / 0 - 22 °C

4: 1.) potassium t-butoxide / THF, 0 deg C, 2 h

With potassium tert-butylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)96516-X

Reference yield:

2-Cyano-3-methyl-succinic acid 1-tert-butyl ester 4-methyl ester (115133-26-1,115133-27-2) → (S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide (115133-38-5)

Guidance literature:

Multi-step reaction with 8 steps

1: Ph₂P(O)ONH₂, CH₃ONa / methanol

2: 55 percent / H₂O₂/NaOH / CH₂Cl₂ / under phase transfer conditions (Bu₄NHSO₄)

3: 90 percent

4: trifluoracetic acid

5: methanol / 5.5 h

6: Et₃N / CH₂Cl₂ / -45 °C

7: tetrahydrofuran / 8 h / 0 - 22 °C

8: 1.) potassium t-butoxide / THF, 0 deg C, 2 h

With sodium hydroxide; O-(diphenylphosphinyl)hydroxylamine; potassium tert-butylate; dihydrogen peroxide; sodium methylate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)96516-X

Reference yield:

2-Amino-2-cyano-3-methyl-succinic acid 1-tert-butyl ester 4-methyl ester (115133-28-3,115133-29-4) → (S)-2-{(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-[(2E,4Z)-1-hydroxy-5-phenyl-penta-2,4-dien-(E)-ylidene]-3,5-dioxo-pyrrolidin-2-yl}-N-methyl-propionamide (115133-38-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 55 percent / H₂O₂/NaOH / CH₂Cl₂ / under phase transfer conditions (Bu₄NHSO₄)

2: 90 percent

3: trifluoracetic acid

4: methanol / 5.5 h

5: Et₃N / CH₂Cl₂ / -45 °C

6: tetrahydrofuran / 8 h / 0 - 22 °C

7: 1.) potassium t-butoxide / THF, 0 deg C, 2 h

With sodium hydroxide; potassium tert-butylate; dihydrogen peroxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)96516-X

upstream raw materials:

(E)-3-phenylpropenal

{2-[(S)-1-[(2S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-hydroxy-5-((S)-1-methylcarbamoyl-ethyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-2-oxo-ethyl}-phosphonic acid diisopropyl ester

(S)-3-Amino-1,4-dimethyl-pyrrolidine-2,5-dione

2-Cyano-3-methyl-succinic acid 1-tert-butyl ester 4-methyl ester