(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

Base Information

Chemical Name:(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile
CAS No.:308240-81-5
Molecular Formula:C₂₇H₄₂N₂O₃SSi
Molecular Weight:502.794
Hs Code.:

Synonyms:(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

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Chemical Property of (S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

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Technology Process of (S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

There total 12 articles about (S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile 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:

: 276870-05-4
(3S)-3-hydroxy-4-(triisopropylsilyloxy)butyric acid methyl ester

: 308240-81-5
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

Guidance literature:: Multi-step reaction with 10 steps

1: 76 percent / CSA / CH₂Cl₂ / 72 h / 20 °C

2: 90 percent / LiOH / tetrahydrofuran; H₂O / 12 h / 20 °C

3: Et₃N / 20 °C

4: NH₄OH / 0.5 h / 20 °C

5: 99 percent / Lawesson's reagent / tetrahydrofuran / 0.5 h / 20 °C

6: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

7: (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.5 h / -30 °C

8: 92 percent / AcOH / tetrahydrofuran; H₂O / 12 h / 20 °C

9: Et₃N / CH₂Cl₂ / 1 h / 0 °C

10: dimethylsulfoxide / 6 h / 60 °C

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; lithium hydroxide; ammonium hydroxide; camphor-10-sulfonic acid; acetic acid; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1: Alkylation / 2: Hydrolysis / 3: Acylation / 4: amidation / 5: Substitution / 6: Cyclization / 7: Dehydration / 8: Elimination / 9: mesylation / 10: Substitution;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

: 308240-90-6
(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone

: 308240-81-5
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: LiHMDS / -78 °C

1.2: 86 percent / TMSCl; Br₂

2.1: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

3.1: (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.5 h / -30 °C

4.1: 92 percent / AcOH / tetrahydrofuran; H₂O / 12 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

6.1: dimethylsulfoxide / 6 h / 60 °C

With pyridine; 2,6-dimethylpyridine; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1.1: deprotonation / 1.2: Bromination / 2.1: Cyclization / 3.1: Dehydration / 4.1: Elimination / 5.1: mesylation / 6.1: Substitution;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

: 308240-79-1
(S)-1-bromo-4-(tert-butyldimethylsilanyloxy)-3-methylbutan-2-one

: 308240-81-5
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

2: (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.5 h / -30 °C

3: 92 percent / AcOH / tetrahydrofuran; H₂O / 12 h / 20 °C

4: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: dimethylsulfoxide / 6 h / 60 °C

With pyridine; 2,6-dimethylpyridine; acetic acid; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1: Cyclization / 2: Dehydration / 3: Elimination / 4: mesylation / 5: Substitution;
DOI:10.1016/S0040-4039(00)01241-7