S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

Base Information

Chemical Name:S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate
CAS No.:370865-56-8
Molecular Formula:C₂₄H₃₀N₂O₅S
Molecular Weight:458.579
Hs Code.:

Synonyms:S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

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Chemical Property of S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

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Technology Process of S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

There total 5 articles about S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate 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%

: 24424-99-5
di-tert-butyl dicarbonate

: 370865-55-7
2-amino-3-benzyloxycarbonylamino-thiobutyric acid S-p-tolyl ester

: 370865-56-8
S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

Guidance literature:: In tetrahydrofuran; for 15h; Heating;
DOI:10.1055/s-2001-16047

Reference yield:

: 150640-22-5
<(4-methylphenyl)thio>nitromethane

: 370865-56-8
S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tBuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

1.2: 75 percent / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

2.1: 84 percent / MeSO₂Cl; iPr₂NEt / CH₂Cl₂ / 5 h / -78 - 20 °C

3.1: tBuOOLi / tetrahydrofuran; toluene; hexane / 1 h / -78 °C

3.2: 53 percent / aq. NH₃ / various solvents / 36 h / 0 °C

4.1: 99 percent / tetrahydrofuran / 24 h / Heating

With potassium tert-butylate; lithium tert-butyl hydroperoxide; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; tert-butyl alcohol; 1.2: Henry reaction;
DOI:10.1055/s-2002-34851

Reference yield:

: 82353-55-7,105499-10-3,141884-07-3,111955-03-4
benzyl (S)-1-oxopropan-2-ylcarbamate

: 370865-56-8
S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tBuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

1.2: 75 percent / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

2.1: 84 percent / MeSO₂Cl; iPr₂NEt / CH₂Cl₂ / 5 h / -78 - 20 °C

3.1: tBuOOLi / tetrahydrofuran; toluene; hexane / 1 h / -78 °C

3.2: 53 percent / aq. NH₃ / various solvents / 36 h / 0 °C

4.1: 99 percent / tetrahydrofuran / 24 h / Heating

With potassium tert-butylate; lithium tert-butyl hydroperoxide; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; tert-butyl alcohol; 1.2: Henry reaction;
DOI:10.1055/s-2002-34851