(4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

Base Information

Chemical Name:(4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one
CAS No.:1311946-54-9
Molecular Formula:C₂₀H₂₀O₄
Molecular Weight:324.376
Hs Code.:

Synonyms:(4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

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Chemical Property of (4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

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Technology Process of (4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

There total 6 articles about (4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one 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: 74.0%

: 1311946-40-3
(4S,5S)-4-(benzyloxy)-5-vinyldihydrofuran-2(3H)-one

: 104713-12-4
(R)-1-phenylprop-2-en-1-ol

: 1311946-54-9
(4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 8h; Inert atmosphere; Reflux;
DOI:10.1016/j.tet.2011.04.014

Reference yield:

: 1169393-30-9
1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol

: 1311946-54-9
(4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: mercury(II) diacetate / tetrahydrofuran; water / 0.5 h / 25 °C

1.2: 0.25 h / 0 °C

1.3: 2.5 h / 0 °C

2.1: dipyridinium dichromate / dichloromethane / 2 h / Molecular sieve; Reflux

3.1: water; acetic acid / 20 °C

4.1: pyridine / 3 h / 0 °C

5.1: sodium iodide / butanone / 12 h / Reflux

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dipyridinium dichromate; mercury(II) diacetate; water; acetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; water; butanone; 6.1: olefin cross metathesis reaction;
DOI:10.1016/j.tet.2011.04.014

Reference yield:

: 1311946-36-7
(4S,5R)-4-(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one

: 1311946-54-9
(4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: water; acetic acid / 20 °C

2: pyridine / 3 h / 0 °C

3: sodium iodide / butanone / 12 h / Reflux

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; water; acetic acid; sodium iodide; In dichloromethane; butanone; 4: olefin cross metathesis reaction;
DOI:10.1016/j.tet.2011.04.014