tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate

Base Information

Chemical Name:tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate
CAS No.:163190-52-1
Molecular Formula:C₃₁H₄₇NO₆Si
Molecular Weight:559.787
Hs Code.:

Synonyms:tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate

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Chemical Property of tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate

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Technology Process of tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate

There total 9 articles about tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate 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: 80.0%

: (2S,4S)-2-tert-Butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid tert-butyl ester

: 163190-52-1
tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate

Guidance literature:: With sodium borodeuteride; In water-d2;
DOI:10.1016/0040-4039(94)02475-Q

Reference yield:

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

: 163190-52-1
tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate

Guidance literature:: Multi-step reaction with 7 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

6: Et₃N / tetrahydrofuran / 1.5 h / -40 °C

7: NaB⁽²⁾H₄ / tetrahydrofuran; D₂O / 1 h / Ambient temperature

With 1H-imidazole; dmap; ruthenium(IV) oxide; lithium hydroxide; sodium hydroxide; sodium periodate; sodium borodeuteride; dimethylsulfide borane complex; dihydrogen peroxide; triethylamine; In tetrahydrofuran; water-d2; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/P19960001131

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 163190-52-1
tert-Butyl (2S,4S)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl<5,5-2H2>pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 34 percent / DMAP, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 15 min, 2.) 2 days

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

3: Et₃N / tetrahydrofuran / 1.5 h / -40 °C

4: NaB⁽²⁾H₄ / tetrahydrofuran; D₂O / 1 h / Ambient temperature

With dmap; lithium hydroxide; sodium borodeuteride; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane; water-d2;
DOI:10.1039/P19960001131