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

Base Information

• Chemical Name: (3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate
• CAS No.: 1287204-74-3
• Molecular Formula: C₂₀H₂₈N₄O₅Se
• Molecular Weight: 483.426

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-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: 58.0%

Phenylselenyl bromide (34837-55-3) + (1S,3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-(trimethylsilyloxy)cyclohexanecarboxylate (1287204-72-1) → (3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate (1287204-74-3)

Guidance literature:

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

(1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate (1287204-65-2) → (3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate (1287204-74-3)

Guidance literature:

Multi-step reaction with 6 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

With titanium(IV) isopropylate; trimethylsilylazide; 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:

(1R,3S,5S,6S)-ethyl 5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptane-3-carboxylate (1287204-68-5) → (3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate (1287204-74-3)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 1 h

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

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

3.2: 0.5 h / -78 °C / Inert atmosphere

3.3: 0.5 h

With titanium(IV) isopropylate; trimethylsilylazide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; benzene;

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

Downstream raw materials:

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

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

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

oseltamivir phosphate

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1287204-74-3 (3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate

Send

Send

Metric Ton KG G Pound L ML

Send

Send