(2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide

Base Information

• Chemical Name: (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide
• CAS No.: 211997-74-9
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411

Synonyms:(2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide

Chemical Property of (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide

Chemical Property:

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Technology Process of (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide

There total 2 articles about (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide 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: 70.0%

(2E,4E)-5-Cyclohexyl-penta-2,4-dienoyl chloride (175552-85-9) + (2S,3R)-5-amino-2,3-epoxy-4,4-dimethoxycyclohex-5-en-1-one (207343-09-7) → (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide (211997-74-9)

Guidance literature:

With lithium tert-butoxide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01047-8

Reference yield:

(2S,3R)-5-tert-butoxycarbonylamino-2,3-epoxy-4,4-dimethoxycyclohex-5-en-1-one (207343-08-6) → (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide (211997-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / TFA / CH₂Cl₂

2: 70 percent / LiOt-Bu / tetrahydrofuran

With trifluoroacetic acid; lithium tert-butoxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(98)01047-8

Reference yield:

(2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide (211997-74-9) → (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,5R,6R)-5-hydroxy-2,2-dimethoxy-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(98)01047-8

upstream raw materials:

(2E,4E)-5-Cyclohexyl-penta-2,4-dienoyl chloride

(2S,3R)-5-amino-2,3-epoxy-4,4-dimethoxycyclohex-5-en-1-one

(2S,3R)-5-tert-butoxycarbonylamino-2,3-epoxy-4,4-dimethoxycyclohex-5-en-1-one

Downstream raw materials:

(2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,5R,6R)-5-hydroxy-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide

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