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

Base Information

Chemical Name:(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate
CAS No.:1287204-69-6
Molecular Formula:C₁₄H₂₄N₄O₅
Molecular Weight:328.368
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-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:

: 1287204-68-5
(1R,3S,5S,6S)-ethyl 5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptane-3-carboxylate

: 1287204-70-9
(1S,3S,4S,5S)-ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate

: 1287204-69-6
(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

Guidance literature:: (1R,3S,5S,6S)-ethyl 5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptane-3-carboxylate; With titanium(IV) isopropylate; trimethylsilylazide; In benzene; at 5 - 20 ℃; for 2h; Inert atmosphere;

With sulfuric acid; water; In benzene; for 1h; regioselective reaction;
DOI:10.1016/j.tet.2011.01.064

Reference yield:

: 1287204-67-4
ethyl (5S)-5-((tert-butoxycarbonyl)amino)cyclohex-3-ene-1-carboxylate

: 1287204-69-6
(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C

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

2.2: 1 h

With titanium(IV) isopropylate; trimethylsilylazide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;
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

: 1287204-69-6
(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 6 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

With titanium(IV) isopropylate; trimethylsilylazide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2-hydroxyethanethiol; diethylazodicarboxylate; In dichloromethane; acetone; toluene; benzene; 3.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2011.01.064