(2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate

Base Information

Chemical Name:(2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate
CAS No.:1353654-56-4
Molecular Formula:C₂₅H₄₂N₂O₆Si
Molecular Weight:494.704
Hs Code.:

Synonyms:(2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate

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Chemical Property of (2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate

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Technology Process of (2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate

There total 8 articles about (2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]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: 24.0%

: 1353654-52-0
(2S,3S)-benzyl 2-amino-5-((tert-butoxycarbonyl)amino)-3-((triethylsilyl)oxy)pentanoate

: 73818-55-0,15596-07-3
Bestmann ylide

: 1353654-53-1
C₁₉H₂₄N₂O₄

: 1353654-56-4
(2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate

Guidance literature:: With benzoic acid; In tetrahydrofuran; at 60 ℃; for 18h; Inert atmosphere;
DOI:10.1016/j.tet.2011.10.099

Reference yield:

: 1175033-05-2
benzyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-2,3-dihydroxypentanoate

: 1353654-53-1
C₁₉H₂₄N₂O₄

: 1353654-56-4
(2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1: dichloromethane / 3 h / Inert atmosphere; Reflux

2: sodium azide; pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

3: 1H-imidazole; dmap / N,N-dimethyl-formamide / 120 h / 20 °C / Inert atmosphere

4: methanol; tin(ll) chloride / 6 h / Inert atmosphere

5: benzoic acid / tetrahydrofuran / 18 h / 60 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; sodium azide; pyridinium p-toluenesulfonate; benzoic acid; tin(ll) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.10.099

Reference yield:

: 1175033-06-3
benzyl (2E)-5-[(tert-butoxycarbonyl)amino]pent-2-enoate

: 1353654-53-1
C₁₉H₂₄N₂O₄

: 1353654-56-4
(2S,3S)-benzyl 2-acetamido-5-(tert-butoxycarbonylamino)-3-[triethylsilyloxy]pentanoate

Guidance literature:: Multi-step reaction with 6 steps

1: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

2: dichloromethane / 3 h / Inert atmosphere; Reflux

3: sodium azide; pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 120 h / 20 °C / Inert atmosphere

5: methanol; tin(ll) chloride / 6 h / Inert atmosphere

6: benzoic acid / tetrahydrofuran / 18 h / 60 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; sodium azide; methanesulfonamide; AD-mix-α; water; pyridinium p-toluenesulfonate; benzoic acid; tin(ll) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tet.2011.10.099