3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 910137-78-9
• Molecular Formula: C₂₅H₃₉NO₇Si
• Molecular Weight: 493.673

Synonyms:3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of 3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 13 articles about 3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl 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: 82.0%

(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (910137-77-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (910137-78-9)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2006.06.117

Reference yield:

(R)-4-((1R,2S)-1,3-Dihydroxy-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (910137-71-2) → 3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (910137-78-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 82 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 91 percent / NaH / dimethylformamide / 0 °C

3: 89 percent / TBAF / tetrahydrofuran / 20 °C

4: 97 percent / Et₃N / CH₂Cl₂ / 20 °C

5: 63 percent / p-TSA / methanol / 20 °C

6: IBX; DMSO / tetrahydrofuran / 20 °C

7: NaOH / tetrahydrofuran; H₂O / 20 °C

8: 85 percent / p-TSA / 20 °C

9: 82 percent / RyCl₃; aq. NaIO₄ / ethyl acetate / 20 °C

10: 86 percent / p-TSA / methanol / 20 °C

11: 82 percent / imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium periodate; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.06.117

Reference yield:

(2S,3R,4S)-3-Benzyloxy-2-formyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1025808-77-8) → 3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (910137-78-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOH / tetrahydrofuran; H₂O / 20 °C

2: 85 percent / p-TSA / 20 °C

3: 82 percent / RyCl₃; aq. NaIO₄ / ethyl acetate / 20 °C

4: 86 percent / p-TSA / methanol / 20 °C

5: 82 percent / imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; sodium hydroxide; sodium periodate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;

DOI:10.1016/j.tetlet.2006.06.117

upstream raw materials:

(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyldimethylsilyl chloride

(R)-4-((1R,2S)-1,3-Dihydroxy-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(2S,3R,4S)-3-Benzyloxy-2-formyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S,3R,4R)-3-Benzoyloxy-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

3-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

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