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

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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}ethanol
CAS No.:1622322-87-5
Molecular Formula:C₃₀H₄₀O₅Si
Molecular Weight:508.73
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}ethanol

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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}ethanol

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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}ethanol

There total 9 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}ethanol 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: 91.0%

: 1622322-61-5
tert-butyldiphenyl{[(R)-1-{(2R,3R)-3-[(1Z,3E)-4-(2-{2-[(triethylsilyl)oxy]ethyl}-1,3-dioxolan-2-yl)buta-1,3-dien-1-yl]oxiran-2-yl}propan-2-yl]oxy}silane

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/ejoc.201402205

Reference yield:

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

: 1622322-87-5
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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 1622322-52-4
tert-butyl({(R)-1-[(2R,3R)-3-ethynyloxiran-2-yl]propan-2-yl}oxy)-diphenylsilane

: 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

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

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

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-nitrobenzenesulfonyl hydrazide; tetrabutyl ammonium fluoride; caesium carbonate; silver nitrate; triethylamine; In tetrahydrofuran; water; isopropyl alcohol; acetone; 3: |Suzuki Coupling;
DOI:10.1002/ejoc.201402205