tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

Base Information

Chemical Name:tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate
CAS No.:163190-43-0
Molecular Formula:C₃₁H₄₃NO₆Si
Molecular Weight:553.771
Hs Code.:

Synonyms:tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

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Technology Process of tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

There total 7 articles about tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate 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: 21.0%

: (S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

: 163190-43-0
tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

: 163190-48-5
tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

Guidance literature:: With ruthenium(IV) oxide; sodium periodate; In ethyl acetate; Ambient temperature;
DOI:10.1039/P19960001131

Reference yield: 12.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 418812-75-6
(S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

: 163190-43-0
tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

: 163190-48-5
tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

Guidance literature:: With dmap; triethylamine; In dichloromethane; 1.) 0 deg C, 15 min, 2.) 2 days;
DOI:10.1039/P19960001131

Reference yield:

: 84348-38-9,1427175-11-8
(S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid

: 163190-43-0
tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / DMAP, Et₃N / acetonitrile / Ambient temperature

2: 1.) Me₂S*BH₃, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 20 deg C, 20 h, 2.) 20 deg C, 2 h

3: 79 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

4: 14 percent / RuO₂*H₂O, aq. NaIO₄ / ethyl acetate / Ambient temperature

With 1H-imidazole; dmap; ruthenium(IV) oxide; sodium hydroxide; sodium periodate; dimethylsulfide borane complex; dihydrogen peroxide; triethylamine; In ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/P19960001131