ethyl (1R,2R,3S,4S)-3-azido-2-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate

Base Information

• Chemical Name: ethyl (1R,2R,3S,4S)-3-azido-2-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate
• CAS No.: 1378923-13-7
• Molecular Formula: C₁₄H₂₄N₄O₅
• Molecular Weight: 328.368
• Mol file: 1378923-13-7.mol

Synonyms:ethyl (1R,2R,3S,4S)-3-azido-2-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about ethyl (1R,2R,3S,4S)-3-azido-2-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate 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: 34.0%

ethyl (1R,2R,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-epoxycyclohexanecarboxylate (1378923-10-4) → ethyl (1R,2R,3R,4R)-4-azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclohexanecarboxylate (1378923-12-6) + ethyl (1R,2R,3S,4S)-3-azido-2-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate (1378923-13-7)

Guidance literature:

With sodium azide; ammonium chloride; In ethanol; water; at 70 ℃; for 4h;

DOI:10.1016/j.tet.2011.12.065

Reference yield:

ethyl (1R,2S)-2-aminocyclohex-3-enecarboxylate hydrochloride (1201815-23-7) → ethyl (1R,2R,3R,4R)-4-azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclohexanecarboxylate (1378923-12-6) + ethyl (1R,2R,3S,4S)-3-azido-2-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate (1378923-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 8 h / 0 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 °C

3: sodium azide; ammonium chloride / ethanol; water / 4 h / 70 °C

With sodium azide; ammonium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1016/j.tet.2011.12.065

Reference yield:

ethyl (1R,2S)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylate (1201815-24-8) → ethyl (1R,2R,3R,4R)-4-azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclohexanecarboxylate (1378923-12-6) + ethyl (1R,2R,3S,4S)-3-azido-2-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate (1378923-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 °C

2: sodium azide; ammonium chloride / ethanol; water / 4 h / 70 °C

With sodium azide; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; water;

DOI:10.1016/j.tet.2011.12.065

upstream raw materials:

ethyl (1R,2S)-2-aminocyclohex-3-enecarboxylate hydrochloride

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

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

di-tert-butyl dicarbonate