(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

Base Information

Chemical Name:(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate
CAS No.:1287204-73-2
Molecular Formula:C₂₀H₂₈N₄O₅Se
Molecular Weight:483.426
Hs Code.:

Synonyms:(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

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Chemical Property of (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

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Technology Process of (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

There total 11 articles about (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate 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: 74.0%

: 34837-55-3
Phenylselenyl bromide

: 1287204-71-0
(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate

: 1287204-73-2
(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

Guidance literature:: (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

Phenylselenyl bromide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; hexane; water; pentane; for 0.5h;
DOI:10.1016/j.tet.2011.01.064

Reference yield:

: 119719-61-8
(1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one

: 1287204-73-2
(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux

2.1: potassium carbonate / 5 h / 20 °C

3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C

6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere

6.2: 1 h

7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 °C / Inert atmosphere

8.3: 0.5 h

With titanium(IV) isopropylate; trimethylsilylazide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2-hydroxyethanethiol; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; benzene; 3.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2011.01.064

Reference yield:

: 1287204-67-4
ethyl (5S)-5-((tert-butoxycarbonyl)amino)cyclohex-3-ene-1-carboxylate

: 1287204-73-2
(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C

2.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere

2.2: 1 h

3.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 °C / Inert atmosphere

4.3: 0.5 h

With titanium(IV) isopropylate; trimethylsilylazide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1016/j.tet.2011.01.064