tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate

Base Information

Chemical Name:tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate
CAS No.:1353654-89-3
Molecular Formula:C₂₈H₄₆N₂O₅Si
Molecular Weight:518.769
Hs Code.:

Synonyms:tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate

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Chemical Property of tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate

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Technology Process of tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate

There total 8 articles about tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate 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: 27.0%

: 1353654-51-9
(2S,3S)-benzyl 2-amino-5-((tert-butoxycarbonyl)amino)-3-((triisopropylsilyl)-oxy)pentanoate

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

: 1353654-89-3
tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate

Guidance literature:: In toluene; for 18h; Inert atmosphere; Reflux;
DOI:10.1016/j.tet.2011.10.099

Reference yield:

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

: 1353654-89-3
tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate

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: toluene / 18 h / Inert atmosphere; Reflux

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

Reference yield:

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

: 1353654-89-3
tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate

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: toluene / 18 h / Inert atmosphere; Reflux

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