tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate

Base Information

Chemical Name:tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate
CAS No.:888949-71-1
Molecular Formula:C₃₅H₅₂N₂O₈S
Molecular Weight:660.872
Hs Code.:

Synonyms:tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate

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Chemical Property of tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate

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Technology Process of tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate

There total 4 articles about tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate 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: 36.0%

: 888949-69-7
(2R,3S)-2,3-bis(benzyloxy)-N-tert-butoxy-4-bromobutyramide

: 630108-94-0
N-tert-butoxycarbonyl-L-homocysteine tert-butyl ester

: 888949-71-1
tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate

Guidance literature:: N-tert-butoxycarbonyl-L-homocysteine tert-butyl ester; With lithium diisopropyl amide; In cyclohexane; N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

(2R,3S)-2,3-bis(benzyloxy)-N-tert-butoxy-4-bromobutyramide; In cyclohexane; N,N-dimethyl-formamide; at 20 ℃; for 48h;
DOI:10.1021/jm060047g

Reference yield:

: 888949-67-5
(2R,3R)-2,3-bis(benzyloxy)-N-tert-butoxy-4-hydroxybutyramide

: 888949-71-1
tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 87 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 20 °C

2.1: LDA / dimethylformamide; cyclohexane / 0.17 h / 0 °C

2.2: 36 percent / dimethylformamide; cyclohexane / 48 h / 20 °C

With carbon tetrabromide; triphenylphosphine; lithium diisopropyl amide; In dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1021/jm060047g

Reference yield:

: 100-39-0
benzyl bromide

: 888949-71-1
tert-butyl (2S)-4-[(2S,3R)-2,3-bis(benzyloxy)-3-tert-butoxycarbamoylpropylmercapto]-2-tert-butoxycarbonylaminobutyrate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Ag₂O / diethyl ether

2.1: 79 percent / AlMe₃ / hexane; CH₂Cl₂ / 20 h / Heating

3.1: 87 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 20 °C

4.1: LDA / dimethylformamide; cyclohexane / 0.17 h / 0 °C

4.2: 36 percent / dimethylformamide; cyclohexane / 48 h / 20 °C

With carbon tetrabromide; trimethylaluminum; triphenylphosphine; silver(l) oxide; lithium diisopropyl amide; In diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1021/jm060047g