(1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid

Base Information

• Chemical Name: (1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
• CAS No.: 1374000-06-2
• Molecular Formula: C₁₈H₂₀O₅S
• Molecular Weight: 348.42

Synonyms:(1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid

Chemical Property of (1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid

Chemical Property:

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Technology Process of (1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid

There total 8 articles about (1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid 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: 87.0%

(1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4-dihydroxycyclohex-2-en-1,5-carbolactone (1259026-05-5) → (1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid (1374000-06-2)

Guidance literature:

(1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4-dihydroxycyclohex-2-en-1,5-carbolactone; With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 0.166667h;

In water; at 20 ℃; pH=6;

DOI:10.1039/c2ob07081b

Reference yield:

3-Bromothianaphthene (7342-82-7) → (1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid (1374000-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: iodine; magnesium / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere; Reflux

1.2: 2 h / Reflux; Inert atmosphere

2.1: tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

3.1: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 12 h / 110 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.1: lithium hydroxide / tetrahydrofuran; water / 0.17 h / 20 °C

5.2: Amberlite IR-120 / 20 °C / pH 6

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; iodine; magnesium; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; 3.1: Suzuki coupling;

DOI:10.1039/c2ob07081b

Reference yield:

(1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4-di(tertbutyldimethylsilyloxy)cyclohex-2-en-1,5-carbolactone (1259026-04-4) → (1R,4R,5R)-3-(3-(benzo[b]thiophen-3-yl)propyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid (1374000-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide / tetrahydrofuran; water / 0.17 h / 20 °C

2.2: Amberlite IR-120 / 20 °C / pH 6

With tetrabutyl ammonium fluoride; lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1039/c2ob07081b

upstream raw materials:

3-Bromothianaphthene

3-allylbenzothiophene

3-[3-(trimethylsilyl)-2-propyn-1-yl]-benzo[b]thiophene

3-(prop-2-ynyl)-1H-benzothiophene

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