(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 262297-18-7
• Molecular Formula: C₂₀H₃₀N₂O₅Si
• Molecular Weight: 406.554

Synonyms:(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Chemical Property of (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

There total 1 articles about (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl 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: 57.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (2S,4R)-2-formyl-4-tert-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (137049-21-9) → (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (262297-18-7)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -70 - 20 ℃; for 1.5h;

DOI:10.1016/S0960-894X(99)00646-0

Reference yield: 47.0%

ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) + (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (262297-18-7) → 5-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

Guidance literature:

With triethylamine; In 1,4-dioxane; dichloromethane; at 20 ℃;

DOI:10.1016/S0960-894X(99)00646-0

Reference yield: 43.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-Methylhydroxylamine (593-77-1) + (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (262297-18-7) → (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-methyl-isoxazolidin-5-yl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:

With sodium acetate; In ethanol; water; for 5h; Heating;

DOI:10.1016/S0960-894X(99)00646-0

upstream raw materials:

Methyltriphenylphosphonium bromide

(2S,4R)-2-formyl-4-tert-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Downstream raw materials:

(2S,4R)-4-Hydroxy-2-(2-methyl-isoxazolidin-5-yl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

(2S,4S)-4-Mercapto-2-(2-methyl-isoxazolidin-5-yl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

(2S,4S)-4-Acetylsulfanyl-2-(2-methyl-isoxazolidin-5-yl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

5-[(2S,4S)-4-Mercapto-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

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