(1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane

Base Information

• Chemical Name: (1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane
• CAS No.: 1449741-42-7
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39
• Mol file: 1449741-42-7.mol

Synonyms:

Chemical Property of (1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane

There total 5 articles about (1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane 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:

(1R,2S)-1-(2-benzyloxy)ethyl-2-hydroxymethylcyclopropane (1449741-40-5) → (1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane (1449741-42-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dess-Martin periodane / dichloromethane / 0.75 h / 0 °C

1.2: 2 h / 20 °C

2.1: triethylamine; diphenyl phosphoryl azide / dichloromethane / 3.5 h / 20 °C

3.1: 19 h / Reflux

With diphenyl phosphoryl azide; Dess-Martin periodane; triethylamine; In dichloromethane; 3.1: |Curtius Rearrangement;

DOI:10.1016/j.bmc.2013.06.063

Reference yield:

(1R,2S)-1-(2-benzyloxy)ethyl-2-carboxycyclopropane (1449741-41-6) → (1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane (1449741-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; diphenyl phosphoryl azide / dichloromethane / 3.5 h / 20 °C

2: 19 h / Reflux

With diphenyl phosphoryl azide; triethylamine; In dichloromethane; 2: |Curtius Rearrangement;

DOI:10.1016/j.bmc.2013.06.063

Reference yield:

(1R,2S)-2-(t-butyldiphenylsilyloxy)methyl-1-(2-hydroxyethyl)cyclopropane (1449741-39-2) → (1R,2S)-1-(2-benzyloxy)ethyl-2-(t-buthoxycarbonyl)aminocyclopropane (1449741-42-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 25 h / -10 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3.1: Dess-Martin periodane / dichloromethane / 0.75 h / 0 °C

3.2: 2 h / 20 °C

4.1: triethylamine; diphenyl phosphoryl azide / dichloromethane / 3.5 h / 20 °C

5.1: 19 h / Reflux

With diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 5.1: |Curtius Rearrangement;

DOI:10.1016/j.bmc.2013.06.063

upstream raw materials:

(1R,2S)-2-(t-butyldiphenylsilyloxy)methyl-1-(2-hydroxyethyl)cyclopropane

(1R,2S)-1-(2-benzyloxy)ethyl-2-hydroxymethylcyclopropane

(1R,2S)-1-(2-benzyloxy)ethyl-2-carboxycyclopropane

benzyl bromide

Downstream raw materials:

tert-butyl [(1S,2R)-2-(2-hydroxyethyl)cyclopropyl]carbamate

(1R,2S)-trans-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane