(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

Base Information

Chemical Name:(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester
CAS No.:909297-59-2
Molecular Formula:C₂₂H₂₃IO₄S
Molecular Weight:510.393
Hs Code.:

Synonyms:(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

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Chemical Property of (2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

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Technology Process of (2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

There total 2 articles about (2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester 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: 96.0%

: 909297-58-1
5-iodo-4-methyl-penta-2,4-dienoic acid

: 253275-90-0
(-)-(1R,2R)-2-(naphthalene-2-sulfonyl)cyclohexanol

: 909297-59-2
(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol061328l

Reference yield:

: 444760-03-6
(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid methyl ester

: 909297-59-2
(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / potassium hydroxide / methanol; H₂O / 2 h / Heating

2: 96 percent / DMAP; DCC / CH₂Cl₂ / 0 - 20 °C

With dmap; potassium hydroxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water;
DOI:10.1021/ol061328l

Reference yield:

: 909297-59-2
(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

: (2E,4Z)-4-Methyl-5-trimethylstannanyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

: 661-69-8
hexamethyldistannane

: 444760-02-5
1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene

: (1S,6R,7R,8S)-1,3,5-Trimethyl-8-(4-nitro-phenyl)-bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

: (1R,6S,7S,8R)-1,3,5-Trimethyl-8-(4-nitro-phenyl)-bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester

Guidance literature:: (2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester; hexamethyldistannane; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene; In benzene; at 70 ℃; for 4h;

(2E,4Z)-4-Methyl-5-trimethylstannanyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester; 1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene; dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 20 ℃; for 12h; Title compound not separated from byproducts;
DOI:10.1021/ol061328l