(4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate

Base Information

Chemical Name:(4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate
CAS No.:854754-90-8
Molecular Formula:C₃₅H₄₁F₃N₂O₈S
Molecular Weight:706.78
Hs Code.:

(4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate

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Chemical Property of (4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate

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Technology Process of (4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate

There total 8 articles about (4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate 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:

: 854754-83-9
(4S)-5-[4-(benzyloxy)phenyl]-4-(dibenzylamino)-3-oxopentanenitrile

: 854754-90-8
(4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran; diethyl ether / 16 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; methanesulfonic acid / tetrahydrofuran; water / 18 h / -10 °C / Inert atmosphere

2.2: 5 h / 0 - 20 °C / Inert atmosphere

3.1: potassium carbonate / tert-butyl methyl ether / 2 h / 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; ammonium formate / tetrahydrofuran / 4 h / Reflux; Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 68 h / 20 °C / Inert atmosphere

6.1: dmap / dichloromethane / 1 h / Reflux; Inert atmosphere

7.1: toluene-4-sulfonic acid; triethylamine / 1 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; methanesulfonic acid; palladium 10% on activated carbon; ammonium formate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl methyl ether; water;
DOI:10.1021/jm201109t

Reference yield:

: 854754-85-1
C₃₉H₄₂N₂O₂

: 854754-90-8
(4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / tert-butyl methyl ether / 2 h / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; ammonium formate / tetrahydrofuran / 4 h / Reflux; Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 68 h / 20 °C / Inert atmosphere

4: dmap / dichloromethane / 1 h / Reflux; Inert atmosphere

5: toluene-4-sulfonic acid; triethylamine / 1 h / 20 °C / Inert atmosphere

With dmap; palladium 10% on activated carbon; ammonium formate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether;
DOI:10.1021/jm201109t

Reference yield:

: 854754-84-0
(2S)-5-amino-1-[4-(benzyloxy)phenyl]-2-(dibenzylamino)-6-phenyl-4-hexen-3-one

: 854754-90-8
(4S,5S)-benzyl 5-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-2,2-dimethyl-4-[4-(trifluoromethylsulfonyloxy)benzyl]oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium tetrahydroborate; methanesulfonic acid / tetrahydrofuran; water / 18 h / -10 °C / Inert atmosphere

1.2: 5 h / 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / tert-butyl methyl ether / 2 h / 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; ammonium formate / tetrahydrofuran / 4 h / Reflux; Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 68 h / 20 °C / Inert atmosphere

5.1: dmap / dichloromethane / 1 h / Reflux; Inert atmosphere

6.1: toluene-4-sulfonic acid; triethylamine / 1 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; methanesulfonic acid; palladium 10% on activated carbon; ammonium formate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether; water;
DOI:10.1021/jm201109t