tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate

Base Information

Chemical Name:tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate
CAS No.:907189-08-6
Molecular Formula:C₃₀H₄₃NO₈
Molecular Weight:545.673
Hs Code.:

Synonyms:tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate

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Chemical Property of tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate

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Technology Process of tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate

There total 7 articles about tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate 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: 86.0%

: 907189-06-4
(S)-2-((2S,4S)-4-tert-butyloxycarbonylmethyl-2-tert-butyl-5-oxo-1,3-dioxolan-4-yl)-3-butenoic acid

: 15100-75-1,75898-47-4
L-phenylalanine tert-butyl ester hydrochloride

: 907189-08-6
tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate

Guidance literature:: With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.1021/jo060931e

Reference yield:

: 907189-03-1
(2S,3S)-2-hydroxy-3-(hydroxycarbonyl)-4-pentenoic acid

: 907189-08-6
tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: i-Pr₂NEt / tetrahydrofuran / 2 h / 25 °C

2.1: 79 percent / Me₃SiOTf / CH₂Cl₂ / 16 h / -35 °C

3.1: lithium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0.83 h / -70 °C

3.2: 61 percent / tetrahydrofuran; dimethylformamide / 0.25 h / -70 °C

4.1: 86 percent / 1-hydroxybenzotriazole; i-Pr₂NEt; HBTU / dimethylformamide / 2 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo060931e

Reference yield:

: 907189-18-8
(2S,3S)-2-hydroxy-3-(hydroxycarbonyl)-4-pentenoate

: 907189-08-6
tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-but-3-enoylamino)-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiOH / methanol; H₂O / 20 °C

2.1: i-Pr₂NEt / tetrahydrofuran / 2 h / 25 °C

3.1: 79 percent / Me₃SiOTf / CH₂Cl₂ / 16 h / -35 °C

4.1: lithium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0.83 h / -70 °C

4.2: 61 percent / tetrahydrofuran; dimethylformamide / 0.25 h / -70 °C

5.1: 86 percent / 1-hydroxybenzotriazole; i-Pr₂NEt; HBTU / dimethylformamide / 2 h / 0 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo060931e