methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

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Chemical Name:methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate
CAS No.:1321925-51-2
Molecular Formula:C₂₁H₄₀N₄O₆Si
Molecular Weight:472.657
Hs Code.:

Synonyms:methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

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Chemical Property of methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

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Technology Process of methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

There total 10 articles about methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate 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: 100.0%

: 1321925-50-1
methyl (1S,2R,4S,5S)-2-(tert-butoxycarbonylamino)-5-(2-chloroethoxy)-4-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate

: 1321925-51-2
methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

Guidance literature:: With sodium azide; iodine; In N,N-dimethyl-formamide; at 50 ℃; for 48h;
DOI:10.1016/j.tet.2011.05.131

Reference yield:

: C₉H₁₁NO₃

: 1321925-51-2
methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: copper(l) chloride / toluene / Reflux

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

3: copper(II) bis(trifluoromethanesulfonate) / 3 h / 40 °C / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C

5: sodium azide; iodine / N,N-dimethyl-formamide / 48 h / 50 °C

With 1H-imidazole; sodium azide; iodine; copper(II) bis(trifluoromethanesulfonate); 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2011.05.131

Reference yield:

: C₉H₁₂O₄

: 1321925-51-2
methyl (1S,2R,4S,5S)-5-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: diphenyl phosphoryl azide; triethylamine / toluene / 80 °C / Inert atmosphere; Reflux

2: copper(l) chloride / toluene / Reflux

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

4: copper(II) bis(trifluoromethanesulfonate) / 3 h / 40 °C / Inert atmosphere

5: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C

6: sodium azide; iodine / N,N-dimethyl-formamide / 48 h / 50 °C

With 1H-imidazole; sodium azide; diphenyl phosphoryl azide; iodine; copper(II) bis(trifluoromethanesulfonate); triethylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Curtius rearrangement;
DOI:10.1016/j.tet.2011.05.131