tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

Base Information

Chemical Name:tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid
CAS No.:163190-51-0
Molecular Formula:C₃₁H₄₅NO₇Si
Molecular Weight:571.786
Hs Code.:

Synonyms:tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

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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,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

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Technology Process of tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

There total 8 articles about tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid 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: 65.0%

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

: 163190-51-0
tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

Guidance literature:: With lithium hydroperoxide; In tetrahydrofuran; water;
DOI:10.1016/0040-4039(94)02475-Q

Reference yield: 57.0%

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

: (S)-5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-2-methylene-5-oxopentanoic acid

: 163190-51-0
tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; 1.) 0 deg C, 15 min, 2.) r.t., 3.5 h;
DOI:10.1039/P19960001131

Reference yield:

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

: 163190-51-0
tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

Guidance literature:: Multi-step reaction with 5 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

5: 57 percent / 60percent H₂O₂, LiOH / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 3.5 h

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