(2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

Base Information

Chemical Name:(2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane
CAS No.:948995-24-2
Molecular Formula:C₃₀H₄₂O₆Si
Molecular Weight:526.745
Hs Code.:

Synonyms:(2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

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Chemical Property of (2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

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Technology Process of (2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

There total 9 articles about (2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane 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: 82.0%

: 948995-23-1
(2R,4S,5R)-5-(2-formylethyl)-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

: 21382-82-1
(carbethoxyethylidene)triphenylphosphorane

: 948995-24-2
(2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

Guidance literature:: In benzene; for 15h;
DOI:10.1021/jo0708442

Reference yield:

: 854490-30-5
(2R,4R,5R)-5-[3-(t-butyldimethylsilyloxy)propyl]-4-formyl-2-phenyl-1,3-dioxane

: 948995-24-2
(2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / LiHMDS; HMPA / tetrahydrofuran; hexane / -78 - 0 °C

2: 93 percent / AcOH / tetrahydrofuran; H₂O / 15 h

3: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4: 82 percent / benzene / 15 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; Dess-Martin periodane; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; benzene; 1: Horner-Wadsworth-Emmons reaction / 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0708442

Reference yield:

: 948995-18-4
methyl (E)-2-(methoxymethoxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynoateprop-2-enoate

: 948995-24-2
(2R,4S,5R)-5-[(3E)-4-(ethoxycarbonyl)pent-3-enyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / DIBAL-H / CH₂Cl₂; toluene / 0.08 h / -78 °C

2: 88 percent / CBr₄; PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

3: 96 percent / acetonitrile / 27 h / Heating

4: 75 percent / LiHMDS; HMPA / tetrahydrofuran; hexane / -78 - 0 °C

5: 93 percent / AcOH / tetrahydrofuran; H₂O / 15 h

6: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7: 82 percent / benzene / 15 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; carbon tetrabromide; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; benzene; 4: Horner-Wadsworth-Emmons reaction / 7: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0708442