(2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl

Base Information

Chemical Name:(2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl
CAS No.:194933-51-2
Molecular Formula:C₂₀H₃₁NO₅Si
Molecular Weight:393.555
Hs Code.:

Synonyms:(2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl

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Chemical Property of (2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl

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Technology Process of (2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl

There total 10 articles about (2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl 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: 99.0%

: 57653-35-7
(2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl

: 18162-48-6
tert-butyldimethylsilyl chloride

: 194933-51-2
(2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 1.5h;

Reference yield: 90.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 13504-86-4
(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline

: 74-88-4
methyl iodide

: 194933-51-2
(2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl

Guidance literature:: (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline; methyl iodide; With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 1h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃;

Reference yield:

: 13504-85-3
(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

: 194933-51-2
(2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl

Guidance literature:: Multi-step reaction with 3 steps

1: 55 percent / Ph₃P; DEAD / tetrahydrofuran / 3 h / 20 °C

2: 99 percent / NaN₃ / 24 h / 45 °C

3: 94 percent / imidiazole / dimethylformamide / 36 h / 20 °C

With 1H-imidazole; sodium azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2005.06.020