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

Base Information

Chemical Name:(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde
CAS No.:308240-93-9
Molecular Formula:C₂₇H₄₃NO₄SSi
Molecular Weight:505.794
Hs Code.:

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

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

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

There total 13 articles about (S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde 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: 85.0%

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

: 308240-93-9
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde

Guidance literature:: With diisobutylaluminium hydride; In toluene; at 0 ℃; for 2h;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

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

: 308240-93-9
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde

Guidance literature:: Multi-step reaction with 11 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

11: 85 percent / DIBAL / toluene / 2 h / 0 °C

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; lithium hydroxide; ammonium hydroxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; 1: Alkylation / 2: Hydrolysis / 3: Acylation / 4: amidation / 5: Substitution / 6: Cyclization / 7: Dehydration / 8: Elimination / 9: mesylation / 10: Substitution / 11: Hydrogenation;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

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

: 308240-93-9
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde

Guidance literature:: Multi-step reaction with 7 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

7.1: 85 percent / DIBAL / toluene / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; 1.1: deprotonation / 1.2: Bromination / 2.1: Cyclization / 3.1: Dehydration / 4.1: Elimination / 5.1: mesylation / 6.1: Substitution / 7.1: Hydrogenation;
DOI:10.1016/S0040-4039(00)01241-7