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

Base Information

Chemical Name:methyl 5-((1'S,2'R)-2-(benzyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate
CAS No.:1338468-26-0
Molecular Formula:C₂₅H₃₅NO₅
Molecular Weight:429.557
Hs Code.:

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

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

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

There total 8 articles about methyl 5-((1'S,2'R)-2-(benzyl(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: 90.0%

: 1338468-13-5
methyl 6-formyl-6-eneoate

: tert-butyl N-benzyl-N-[(1E)-buta-1.3-dienyl]carbamate

: 1338468-26-0
methyl 5-((1'S,2'R)-2-(benzyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate

Guidance literature:: With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; In dichloromethane; at -78 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.08.026

Reference yield:

: 100-46-9
benzylamine

: 1338468-26-0
methyl 5-((1'S,2'R)-2-(benzyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate

Guidance literature:: Multi-step reaction with 6 steps

1: dichloromethane / 2 h / Inert atmosphere

2: dichloromethane / 0 - 20 °C / Inert atmosphere

3: methanol; sodium tetrahydroborate / 1.25 h / 0 - 20 °C

4: pyridine; dmap / acetonitrile / 1 h / 0 - 20 °C / Molecular sieve

5: triethylamine / acetonitrile / 1.5 h / Reflux

6: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate / dichloromethane / -78 - 20 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium tetrahydroborate; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; triethylamine; In dichloromethane; acetonitrile; 6: Diels-Alder reaction;
DOI:10.1016/j.tet.2011.08.026

Reference yield:

: 1338468-23-7
(E)-tert-butyl benzyl(3-oxobut-1-en-1-yl)carbamate

: 1338468-26-0
methyl 5-((1'S,2'R)-2-(benzyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: methanol; sodium tetrahydroborate / 1.25 h / 0 - 20 °C

2: pyridine; dmap / acetonitrile / 1 h / 0 - 20 °C / Molecular sieve

3: triethylamine / acetonitrile / 1.5 h / Reflux

4: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate / dichloromethane / -78 - 20 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium tetrahydroborate; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; triethylamine; In dichloromethane; acetonitrile; 4: Diels-Alder reaction;
DOI:10.1016/j.tet.2011.08.026