tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

Base Information

Chemical Name:tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate
CAS No.:1372805-36-1
Molecular Formula:C₁₉H₂₉N₃O₇S
Molecular Weight:443.521
Hs Code.:

Synonyms:tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

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Chemical Property of tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

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Technology Process of tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

There total 7 articles about tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate 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: 66.0%

: 1372805-34-9
methyl (R)-2-[(1r,4R)-4-(tert-butoxycarbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate

: 1372805-36-1
tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -10 - 0 ℃; for 2.5h; Inert atmosphere;
DOI:10.1055/s-0031-1289724

Reference yield:

: 1372805-32-7
methyl (R)-2-[(1s,4S)-4-hydroxycyclohexyl]-2-(2-nitrophenylsulfonamido)acetate

: 1372805-36-1
tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 1.5 h / 5 - 20 °C / Inert atmosphere; Large scale reaction

2.1: sodium azide / N,N-dimethyl-formamide / 16 h / 55 °C / Large scale reaction

3.1: triphenylphosphine / ethyl acetate / 1.5 h / 65 °C / Large scale reaction

3.2: 1.5 h / 65 °C / Large scale reaction

4.1: triethylamine / dichloromethane / 18 h / 25 °C / Large scale reaction

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -10 - 0 °C / Inert atmosphere

With sodium azide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-0031-1289724

Reference yield:

: 1372805-33-8
methyl (R)-2-[(1s,4S)-4-(methylsulfonyloxy)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate

: 1372805-36-1
tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium azide / N,N-dimethyl-formamide / 16 h / 55 °C / Large scale reaction

2.1: triphenylphosphine / ethyl acetate / 1.5 h / 65 °C / Large scale reaction

2.2: 1.5 h / 65 °C / Large scale reaction

3.1: triethylamine / dichloromethane / 18 h / 25 °C / Large scale reaction

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -10 - 0 °C / Inert atmosphere

With sodium azide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-0031-1289724