(S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate

Base Information

Chemical Name:(S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate
CAS No.:1434564-48-3
Molecular Formula:C₂₅H₃₃NO₆Si
Molecular Weight:471.626
Hs Code.:

Synonyms:(S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate

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Chemical Property of (S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate

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Technology Process of (S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate

There total 5 articles about (S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate 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: 69.0%

: 909019-16-5
benzyl (tert‐butyldimethylsilyl)oxycarbamate

: 162398-42-7
(E)-benzyl 4-oxobut-2-enoate

: 1434564-48-3
(S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate

Guidance literature:: benzyl (tert‐butyldimethylsilyl)oxycarbamate; With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid; In chloroform; at 20 ℃; for 0.166667h;

(E)-benzyl 4-oxobut-2-enoate; In chloroform; at 20 ℃; for 3.5h;
DOI:10.1021/jo400558t

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1434564-48-3
(S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / chloroform / 0.17 h / 20 °C

2.2: 3.5 h / 20 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid; triethylamine; In dichloromethane; chloroform;
DOI:10.1021/jo400558t

Reference yield:

: 7396-44-3
benzyl diethylphosphonoacetate

: 1434564-48-3
(S)-benzyl 2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)]amino-4-oxobutanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: caesium carbonate / cyclohexane / 65 °C

1.2: 2 h / 65 °C

2.1: hydrogenchloride / acetone; water / 48 h / 20 °C

3.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / chloroform / 0.17 h / 20 °C

3.2: 3.5 h / 20 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; hydrogenchloride; caesium carbonate; acetic acid; In chloroform; cyclohexane; water; acetone; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/jo400558t