2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid

Base Information

• Chemical Name: 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid
• CAS No.: 1262235-04-0
• Molecular Formula: C₂₃H₃₂O₈
• Molecular Weight: 436.502

Synonyms:2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid

Chemical Property of 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid

Chemical Property:

Purity/Quality:

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Technology Process of 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid

There total 6 articles about 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic 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: 96.0%

2-(trimethylsilyl)ethyl 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoate (1262235-13-1) → 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid (1262235-04-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.10.092

Reference yield:

((4R,5S)-5-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl pivalate (603039-01-6) → 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid (1262235-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium; diethylamine / tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane / 0.17 h / -78 °C / Inert atmosphere

1.2: 0.17 h / -78 °C / Inert atmosphere

2.1: dihydrogen peroxide / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

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

With n-butyllithium; tetrabutyl ammonium fluoride; dihydrogen peroxide; diethylamine; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane; water;

DOI:10.1016/j.tetlet.2010.10.092

Reference yield:

((4R,5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl pivalate (603039-00-5) → 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoic acid (1262235-04-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium; diethylamine / tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane / 0.17 h / -78 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

3.1: dihydrogen peroxide / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

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

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; diethylamine; triphenylphosphine; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane; water;

DOI:10.1016/j.tetlet.2010.10.092

upstream raw materials:

((4R,5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl pivalate

((4R,5S)-5-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl pivalate

2-(trimethylsilyl)ethyl 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoate

C₁₃H₂₂O₅

Downstream raw materials:

(S,Z)-5-iodopent-4-en-2-yl 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoate

(S,Z)-5-bromopent-4-en-2-yl 2-((E)-3-((4S,5R)-2,2-dimethyl-5-(pivaloyloxymethyl)-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoate

(S,Z)-5-bromopent-4-en-2-yl 2-((E)-3-((4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoate

(S,Z)-5-iodopent-4-en-2-yl 2-((E)-3-((4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl)-4,6-dimethoxybenzoate

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