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

Base Information

Chemical Name:methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate
CAS No.:1321925-49-8
Molecular Formula:C₁₅H₂₆ClNO₆
Molecular Weight:351.828
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-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: 74.0%

: 1321925-41-0
methyl (1S,2R,4S,5R)-2-(tert-butoxycarbonylamino)-4,5-epoxycyclohexanecarboxylate

: 107-07-3
2-chloro-ethanol

: 1321925-49-8
methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate

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

Guidance literature:: With copper(II) bis(trifluoromethanesulfonate); at 40 ℃; for 3h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.131

Reference yield:

: C₉H₁₂O₄

: 1321925-49-8
methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: C₈H₁₁N*C₉H₁₂O₄

: 1321925-49-8
methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogenchloride / water

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

3: copper(l) chloride / toluene / Reflux

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

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

With hydrogenchloride; diphenyl phosphoryl azide; copper(II) bis(trifluoromethanesulfonate); triethylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; In dichloromethane; water; toluene; 2: Curtius rearrangement;
DOI:10.1016/j.tet.2011.05.131