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

Base Information

• Chemical Name: (3S,4S,5S)-ethyl 5-azido-3-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate
• CAS No.: 1287204-77-6
• Molecular Formula: C₁₄H₂₂N₄O₅
• Molecular Weight: 326.352

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3S,4S,5S)-ethyl 5-azido-3-(tert-butoxycarbonylamino)-4-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:

(3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate (1287204-74-3) → (3S,4S,5S)-ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate (950690-25-2) + (3S,4S,5S)-ethyl 5-azido-3-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate (1287204-77-6)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2011.01.064

Reference yield:

(1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one (119719-61-8) → (3S,4S,5S)-ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate (950690-25-2) + (3S,4S,5S)-ethyl 5-azido-3-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate (1287204-77-6)

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

Reference yield:

(1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate (1287204-65-2) → (3S,4S,5S)-ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate (950690-25-2) + (3S,4S,5S)-ethyl 5-azido-3-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate (1287204-77-6)

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

upstream raw materials:

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

(1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate

(1R,5S)-ethyl 5-(N-(tert-butoxycarbonyl)-4-nitrophenylsulfonamido)cyclohex-3-enecarboxylate

ethyl (5S)-5-((tert-butoxycarbonyl)amino)cyclohex-3-ene-1-carboxylate

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