(2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone

Base Information

• Chemical Name: (2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone
• CAS No.: 796866-73-4
• Molecular Formula: C₁₃H₁₇IO₃
• Molecular Weight: 348.181

Synonyms:(2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone

Chemical Property of (2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone

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Technology Process of (2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone

There total 2 articles about (2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone 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: 62.0%

(2R,2'S)-2-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]-4-methyl-2-(4'-pentenyl)-cyclohex-3-en-1-one (796866-69-8) → (2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone (796866-73-4)

Guidance literature:

With iodine; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/jo0490853

Reference yield:

(2'S,6R)-6-(4'-pentenyl)-1-methoxy-6-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]-4-methyl-1,4-cyclohexadiene (796866-64-3) → (2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone (796866-73-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / aq. HCl / methanol / 3 h / 20 °C

2: 62 percent / I₂ / tetrahydrofuran; H₂O / 20 °C

With hydrogenchloride; iodine; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo0490853

Reference yield: 81.0%

(2R,3R,4R)-3-iodo-4-methyl-1-oxo-2-(pent-4-en-1-yl)cyclohexane-2,4-carbolactone (796866-73-4) → (4R)-4-hydroxy-4-methyl-2-(pent-4-en-1-yl)-2-cyclohexen-1-one + (5R)-5-[(2'-hydroxycarbonyl)ethyl]-3-(pent-4-en-1-yl)-5-methylfuran-2(5H)-one

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo0490853

upstream raw materials:

(2R,2'S)-2-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]-4-methyl-2-(4'-pentenyl)-cyclohex-3-en-1-one

(2'S,6R)-6-(4'-pentenyl)-1-methoxy-6-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]-4-methyl-1,4-cyclohexadiene

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