(2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester

Base Information

• Chemical Name: (2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester
• CAS No.: 500103-05-9
• Molecular Formula: C₃₅H₅₀O₄Si₂
• Molecular Weight: 590.951

Synonyms:(2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester

Chemical Property of (2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester

There total 7 articles about (2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester 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: 100.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (2R,3R)-5-Hydroxy-3-methyl-2-triphenylsilanyloxy-pentanoic acid ethyl ester (500103-04-8) → (2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester (500103-05-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

Triphenylsilyl chloride (76-86-8) → (2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester (500103-05-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / imidazole; 4-(N,N-dimethylamino)pyridine / dimethylformamide / 0 °C

2: 95 percent / Et₃SiH / Pd/C / acetone

3: 84 percent / Zn; [(cyclopentadienyl)2ZrCl₂] / tetrahydrofuran / 0 °C

4: [(Ph₃P)3RhCl] / tetrahydrofuran / 0 °C

5: H₂O₂ / ethanol / pH 7

6: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; Wilkinson's catalyst; zirconocene dichloride; dihydrogen peroxide; zinc; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

(2R,3S)-2-Hydroxy-3-phenylsulfanylcarbonyl-butyric acid ethyl ester (246510-31-6) → (2R,3R)-3-Methyl-5-triisopropylsilanyloxy-2-triphenylsilanyloxy-pentanoic acid ethyl ester (500103-05-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / imidazole; 4-(N,N-dimethylamino)pyridine / dimethylformamide / 0 °C

2: 95 percent / Et₃SiH / Pd/C / acetone

3: 84 percent / Zn; [(cyclopentadienyl)2ZrCl₂] / tetrahydrofuran / 0 °C

4: [(Ph₃P)3RhCl] / tetrahydrofuran / 0 °C

5: H₂O₂ / ethanol / pH 7

6: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; Wilkinson's catalyst; zirconocene dichloride; dihydrogen peroxide; zinc; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(2R,3R)-5-Hydroxy-3-methyl-2-triphenylsilanyloxy-pentanoic acid ethyl ester

Triphenylsilyl chloride

(2R,3S)-2-Hydroxy-3-phenylsulfanylcarbonyl-butyric acid ethyl ester

Downstream raw materials:

(1R,2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2S,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-methyl-5-triisopropylsilanyloxy-pentan-1-ol

(2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol

(2R,3R)-2-[(2R,3R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxirane

(1R,2R,3R)-1-[(2S,4R,5S)-5-(Benzothiazole-2-sulfonylmethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-5-triisopropylsilanyloxy-pentan-1-ol

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