benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

Base Information

Chemical Name:benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate
CAS No.:1338487-69-6
Molecular Formula:C₁₉H₁₉NO₃Se
Molecular Weight:388.325
Hs Code.:

Synonyms:benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

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Chemical Property of benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

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Technology Process of benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

There total 4 articles about benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-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:

: 1338487-68-5
benzyl (1S,3S,5S)-2-oxo-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

: 1338487-69-6
benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; water; at -78 ℃; for 0.5h; optical yield given as %ee;
DOI:10.1021/ol2023054

Reference yield:

: 930-30-3
cyclopent-2-enone

: 1338487-69-6
benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: C₁₉H₂₆N₂; sodium hydrogencarbonate; benzoic acid / chloroform / 40 h / 20 °C

2.1: N,O-bis-(trimethylsilyl)-acetamide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 20 °C

2.2: 0.83 h / -78 °C

3.1: sodium tetrahydroborate / tetrahydrofuran; water / 0.5 h / -78 °C

With sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; C₁₉H₂₆N₂; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzoic acid; In tetrahydrofuran; chloroform; water; toluene;
DOI:10.1021/ol2023054

Reference yield:

: 64420-86-6
O-p-toluenesulfonyl benzyloxyhydroxamate

: 1338487-69-6
benzyl (1S,2S,3S,5S)-2-hydroxy-3-(phenylselanyl)-6-azabicyclo[3.1.0]hexane-6-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: C₁₉H₂₆N₂; sodium hydrogencarbonate; benzoic acid / chloroform / 40 h / 20 °C

2.1: N,O-bis-(trimethylsilyl)-acetamide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 20 °C

2.2: 0.83 h / -78 °C

3.1: sodium tetrahydroborate / tetrahydrofuran; water / 0.5 h / -78 °C

With sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; C₁₉H₂₆N₂; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzoic acid; In tetrahydrofuran; chloroform; water; toluene;
DOI:10.1021/ol2023054