(E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester
CAS No.:476687-75-9
Molecular Formula:C₂₂H₂₈O₇
Molecular Weight:404.46
Hs Code.:

Synonyms:(E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

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Chemical Property of (E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

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Technology Process of (E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

There total 11 articles about (E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester 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:

: 623-47-2
propynoic acid ethyl ester

: 4-((4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butan-2-one

: 476687-75-9
(E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃;
DOI:10.1021/ol026804w

Reference yield:

: 50907-65-8
2-deoxy-D-erythro-pentose cyclic 1,3-propanediyl mercaptal

: 476687-75-9
(E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: CSA / CH₂Cl₂ / 20 °C

2.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

3.1: 98 percent / MeI; NaHCO₃ / H₂O; acetonitrile / 20 °C

4.1: 95 percent / SmI₂ / methanol; tetrahydrofuran / 0 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

6.1: DIBAH / CH₂Cl₂ / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

8.1: NaI / acetone / 60 °C

9.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

9.2: 100 percent / SiO₂; H₂O

10.1: TBAF / tetrahydrofuran / 20 °C

11.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; acetonitrile; 2.1: hetero-Michael reaction / 11.1: hetero-Michael reaction;
DOI:10.1021/ol026804w

Reference yield:

: 476687-71-5
((4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-acetic acid ethyl ester

: 476687-75-9
(E)-3-[(4aR,6S,7R,8aS)-6-(3-Oxo-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: DIBAH / CH₂Cl₂ / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

4.1: NaI / acetone / 60 °C

5.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

5.2: 100 percent / SiO₂; H₂O

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone; 7.1: hetero-Michael reaction;
DOI:10.1021/ol026804w