methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate

Base Information

• Chemical Name: methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate
• CAS No.: 1338468-32-8
• Molecular Formula: C₂₀H₃₃NO₅
• Molecular Weight: 367.486
• Mol file: 1338468-32-8.mol

Synonyms:methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate

Chemical Property of methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate

There total 4 articles about methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate 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:

methyl 6-formyl-6-eneoate (1338468-13-5) + (E)-tert-butyl buta-1,3-dienyl(ethyl)carbamate (1338468-17-9) → methyl 5-((1'R,2'S)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate + methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate (1338468-32-8)

Guidance literature:

With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; In dichloromethane; for 3h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.08.026

Reference yield:

methyl 7-oxoheptanoate (35376-00-2) → methyl 5-((1'R,2'S)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate + methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate (1338468-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyrrolidine propionic acid salt / water; isopropyl alcohol / 50 °C / Inert atmosphere

2: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate / dichloromethane / 3 h / Inert atmosphere

With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; pyrrolidine propionic acid salt; In dichloromethane; water; isopropyl alcohol;

DOI:10.1016/j.tet.2011.08.026

Reference yield:

Cycloheptene (628-92-2,45509-99-7) → methyl 5-((1'R,2'S)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate + methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate (1338468-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate; ozone / dichloromethane

1.2: Inert atmosphere

2.1: pyrrolidine propionic acid salt / water; isopropyl alcohol / 50 °C / Inert atmosphere

3.1: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate / dichloromethane / 3 h / Inert atmosphere

With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; pyrrolidine propionic acid salt; sodium hydrogencarbonate; ozone; In dichloromethane; water; isopropyl alcohol;

DOI:10.1016/j.tet.2011.08.026

upstream raw materials:

methyl 6-formyl-6-eneoate

(E)-tert-butyl buta-1,3-dienyl(ethyl)carbamate

methyl 7-oxoheptanoate

Cycloheptene

Refernces