2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde

Base Information

Chemical Name:2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde
CAS No.:1622322-43-3
Molecular Formula:C₃₀H₃₈O₅Si
Molecular Weight:506.714
Hs Code.:

Synonyms:2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde

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Chemical Property of 2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde

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Technology Process of 2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde

There total 11 articles about 2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde 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: 83.0%

: 1622322-87-5
2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl]oxiran-2-yl}buta-1,3-dien-1-yl]-1,3-dioxolan-2-yl}ethanol

: 1622322-43-3
2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;
DOI:10.1002/ejoc.201402205

Reference yield:

: 303044-46-4
(-)-(2R,3R,5R)-5-(tert-butyldiphenylsilyloxy)-2,3-(oxiranyl)-hexan-1-al

: 1622322-43-3
2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: potassium carbonate / methanol / 3 h / 0 °C / Inert atmosphere

2: N-iodo-succinimide; silver nitrate / acetone / 1 h / 25 °C / Inert atmosphere; Darkness

3: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 40 h / 25 °C / Inert atmosphere; Darkness

4: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 7 h / 55 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

6: Dess-Martin periodane / dichloromethane / 2 h / 25 °C / Inert atmosphere

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-nitrobenzenesulfonyl hydrazide; tetrabutyl ammonium fluoride; potassium carbonate; caesium carbonate; Dess-Martin periodane; silver nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; acetone; 4: |Suzuki Coupling;
DOI:10.1002/ejoc.201402205

Reference yield:

: 1622322-54-6
tert-butyl({(R)-1-[(2R,3R)-3-(iodoethynyl)oxiran-2-yl]propan-2-yl}oxy)diphenylsilane

: 1622322-43-3
2-{2-[(1E,3Z)-4-{(2R,3R)-3-[(R)-2-(tert-butyldiphenylsilyloxy)-propyl ]oxiran-2-yl}buta-1,3-dien-1-yl ]-1,3-dioxolan-2-yl}acetaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 40 h / 25 °C / Inert atmosphere; Darkness

2: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 7 h / 55 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4: Dess-Martin periodane / dichloromethane / 2 h / 25 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-nitrobenzenesulfonyl hydrazide; tetrabutyl ammonium fluoride; caesium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; 2: |Suzuki Coupling;
DOI:10.1002/ejoc.201402205