(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate

Base Information

Chemical Name:(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate
CAS No.:1287204-76-5
Molecular Formula:C₁₄H₂₂N₄O₅
Molecular Weight:326.352
Hs Code.:

Synonyms:(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate

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Chemical Property of (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate

Chemical Property:

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Technology Process of (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate

There total 11 articles about (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate 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:

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

: 1287204-76-5
(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate

: 1287204-75-4
(3R,4R,5S)-ethyl-4-azido-5-(tert-butoxycarbonylamino)-3-hydroxycyclohex-1-enecarboxylate

Guidance literature:: With pyridine; dihydrogen peroxide; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/j.tet.2011.01.064

Reference yield:

: 1287204-65-2
(1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate

: 1287204-76-5
(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

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

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C

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

4.2: 1 h

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

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

6.2: 0.5 h / -78 °C / Inert atmosphere

6.3: 0.5 h

7.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C

With pyridine; titanium(IV) isopropylate; trimethylsilylazide; dihydrogen peroxide; 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; 1.1: Mitsunobu reaction;
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

: 1287204-76-5
(3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 9 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

9.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C

With pyridine; titanium(IV) isopropylate; trimethylsilylazide; dihydrogen peroxide; 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