4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole

Base Information

• Chemical Name: 4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole
• CAS No.: 308240-80-4
• Molecular Formula: C₃₂H₅₇NO₄SSi₂
• Molecular Weight: 608.046

Synonyms:4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole

Chemical Property of 4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole

Chemical Property:

Purity/Quality:

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Technology Process of 4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole

There total 12 articles about 4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole 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:

4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-4,5-dihydro-thiazol-4-ol → 4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole (308240-80-4)

Guidance literature:

With pyridine; trifluoroacetic anhydride; In dichloromethane; at -30 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester (93454-85-4) → 4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole (308240-80-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 61 percent / AlMe₃ / CH₂Cl₂ / 5 h / Heating

2.1: 94 percent / tetrahydrofuran / 1 h / 0 °C

3.1: LiHMDS / -78 °C

3.2: 86 percent / TMSCl; Br₂

4.1: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

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

With pyridine; 2,6-dimethylpyridine; trimethylaluminum; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.1: Substitution / 2.1: Grignard reaction / 3.1: deprotonation / 3.2: Bromination / 4.1: Cyclization / 5.1: Dehydration;

DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

(3S)-3-hydroxy-4-(triisopropylsilyloxy)butyric acid methyl ester (276870-05-4) → 4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole (308240-80-4)

Guidance literature:

Multi-step reaction with 7 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

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; lithium hydroxide; ammonium hydroxide; camphor-10-sulfonic acid; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; 1: Alkylation / 2: Hydrolysis / 3: Acylation / 4: amidation / 5: Substitution / 6: Cyclization / 7: Dehydration;

DOI:10.1016/S0040-4039(00)01241-7

upstream raw materials:

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester

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

tert-butyldimethylsilyl chloride

(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone

Downstream raw materials:

(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

(3R,5S)-3-Amino-5-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

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