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

Base Information

Chemical Name:methyl (1S,2R,4S,5S)-2-(tert-butoxycarbonylamino)-5-(2-chloroethoxy)-4-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate
CAS No.:1321925-50-1
Molecular Formula:C₂₁H₄₀ClNO₆Si
Molecular Weight:466.09
Hs Code.:

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

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

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

There total 9 articles about methyl (1S,2R,4S,5S)-2-(tert-butoxycarbonylamino)-5-(2-chloroethoxy)-4-(tert-butyldimethylsilanyloxy)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: 89.0%

: 1321925-48-7
methyl (1S,2R,4S,5S)-2-(tert-butoxycarbonylamino)-5-(2-chloroethoxy)-4-hydroxycyclohexanecarboxylate

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1016/j.tet.2011.05.131

Reference yield:

: C₉H₁₂O₄

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

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; diphenyl phosphoryl azide; 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

Reference yield:

: C₉H₁₁NO₃

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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; 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