ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate

Base Information

• Chemical Name: ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate
• CAS No.: 1337970-90-7
• Molecular Formula: C₁₄H₂₃NO₅
• Molecular Weight: 285.34
• Mol file: 1337970-90-7.mol

Synonyms:ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate

Chemical Property of ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate

There total 5 articles about ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-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: 66.0%

ethanol (64-17-5) + tert-butyl (1R,5R,8R)-7-oxo-6-oxabicyclo[3.2.1]oct-3-en-8-ylcarbamate → ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate (1337970-90-7)

Guidance literature:

With sodium ethanolate; at 20 ℃; for 9h;

DOI:10.1039/c1ob05648d

Reference yield:

(1R,2S)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid (870288-16-7,233600-33-4) → ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate (1337970-90-7)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water / 16 h / 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 6 h / 65 °C

3: sodium ethanolate / 9 h / 20 °C

With iodine; sodium ethanolate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c1ob05648d

Reference yield:

tert-butyl (1R,4R,5S,8R)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]octan-8-ylcarbamate → ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate (1337970-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 6 h / 65 °C

2: sodium ethanolate / 9 h / 20 °C

With sodium ethanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1039/c1ob05648d

upstream raw materials:

(1R,2S)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid

ethanol

(1R,2S)-cis-2-aminocyclohex-3-enecarboxylic acid

Downstream raw materials:

ethyl (1S,2S)-2-(tert-butoxycarbonylamino)yclohex-3-enecarboxylate

ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate

ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohexanecarboxylate