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

Base Information

Chemical Name:(1S,3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-(trimethylsilyloxy)cyclohexanecarboxylate
CAS No.:1287204-72-1
Molecular Formula:C₁₇H₃₂N₄O₅Si
Molecular Weight:400.55
Hs Code.:

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

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

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

There total 9 articles about (1S,3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-(trimethylsilyloxy)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: 94.0%

: 75-77-4
chloro-trimethyl-silane

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

: 1287204-72-1
(1S,3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-(trimethylsilyloxy)cyclohexanecarboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tet.2011.01.064

Reference yield:

: 1287204-65-2
(1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate

: 1287204-72-1
(1S,3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-(trimethylsilyloxy)cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 5 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

With titanium(IV) isopropylate; trimethylsilylazide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2-hydroxyethanethiol; diethylazodicarboxylate; In dichloromethane; acetone; toluene; benzene; 1.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2011.01.064

Reference yield:

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

: 1287204-72-1
(1S,3S,4S,5S)-ethyl-3-azido-5-(tert-butoxycarbonylamino)-4-(trimethylsilyloxy)cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 2 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

With titanium(IV) isopropylate; trimethylsilylazide; triethylamine; In dichloromethane; benzene;
DOI:10.1016/j.tet.2011.01.064