(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

Base Information

Chemical Name:(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
CAS No.:1262235-15-3
Molecular Formula:C₂₃H₃₁BrO₇
Molecular Weight:499.399
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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%

: 1262235-14-2
(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

: 1262235-15-3
(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

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.tetlet.2010.10.092

Reference yield:

: 603039-00-5
((4R,5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl pivalate

: 1262235-15-3
(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

Guidance literature:: Multi-step reaction with 6 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

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

6.1: sodium methylate / methanol / 3 h / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; sodium methylate; diethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane; water; 5.1: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2010.10.092

Reference yield:

: C₃₄H₅₀O₈SeSi

: 1262235-15-3
(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

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

4: sodium methylate / methanol / 3 h / 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; triphenylphosphine; In tetrahydrofuran; methanol; water; 3: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2010.10.092