(S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide

Base Information

• Chemical Name: (S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide
• CAS No.: 1401113-13-0
• Molecular Formula: C₂₃H₂₈N₂O₆
• Molecular Weight: 428.485

Synonyms:(S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide

Chemical Property of (S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide

There total 8 articles about (S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide 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: 79.0%

5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide (1401113-06-1) + (S,E)-4-(benzyloxy)-1-bromo-7-methoxyhept-5-en-2-one (1401113-07-2) → (S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide (1401113-13-0)

Guidance literature:

With caesium carbonate; In acetonitrile; at 0 ℃; for 8.5h; Inert atmosphere;

DOI:10.1021/jo301835e

Reference yield:

(R,E)-ethyl-4-(benzyloxy)-5-hydroxypent-2-enoate → (S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide (1401113-13-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.5 h / 45 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.75 h / 0 °C / Inert atmosphere

3.1: sodium hydride; tert-butyl alcohol / N,N-dimethyl-formamide / 0.92 h / 0 °C

3.2: 5 h / 0 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere

5.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; water / 0.75 h / 0 °C / Inert atmosphere

6.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / Inert atmosphere

7.1: caesium carbonate / acetonitrile / 8.5 h / 0 °C / Inert atmosphere

With lithium aluminium tetrahydride; carbon tetrabromide; sodium hydride; caesium carbonate; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo301835e

Reference yield:

(R,E)-4-(benzyloxy)-5-bromopent-2-en-1-ol (1401113-08-3) → (S,E)-1-(4-(benzyloxy)-7-methoxy-2-oxohept-5-en-1-yl)-5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide (1401113-13-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

1.2: 0.75 h / 0 °C / Inert atmosphere

2.1: sodium hydride; tert-butyl alcohol / N,N-dimethyl-formamide / 0.92 h / 0 °C

2.2: 5 h / 0 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere

4.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; water / 0.75 h / 0 °C / Inert atmosphere

5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / Inert atmosphere

6.1: caesium carbonate / acetonitrile / 8.5 h / 0 °C / Inert atmosphere

With lithium aluminium tetrahydride; carbon tetrabromide; sodium hydride; caesium carbonate; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo301835e

upstream raw materials:

5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide

(S,E)-4-(benzyloxy)-1-bromo-7-methoxyhept-5-en-2-one

(R,E)-4-(benzyloxy)-5-bromopent-2-en-1-ol

1H-pyrrole-2-carboxylic acid methoxymethylamide

Downstream raw materials:

(2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-N-methoxy-Nmethyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c]-[1,4]oxazine]-6′-carboxamide

(2R,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-N-methoxy-Nmethyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c]-[1,4]oxazine]-6′-carboxamide

(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

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