(2R,4S,5R)-5-[3-(tert-butyldimethylsilyloxy)propyl]-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-[3-(tert-butyldimethylsilyloxy)propyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane
CAS No.:948995-21-9
Molecular Formula:C₃₁H₅₀O₅Si₂
Molecular Weight:558.906
Hs Code.:

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

There total 5 articles about (2R,4S,5R)-5-[3-(tert-butyldimethylsilyloxy)propyl]-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: 75.0%

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

: 948995-04-8
diethyl (E)-1-bromo-2-(methoxymethoxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynyl phosphonate

: 948995-21-9
(2R,4S,5R)-5-[3-(tert-butyldimethylsilyloxy)propyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 - 0 ℃;
DOI:10.1021/jo0708442

Reference yield:

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

: 948995-21-9
(2R,4S,5R)-5-[3-(tert-butyldimethylsilyloxy)propyl]-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: 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; carbon tetrabromide; diisobutylaluminium hydride; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0708442

Reference yield:

: 948995-19-5
(E)-2-(methoxymethoxymethyl)-5-(trimethylsilyl)pent-2-en-4-yn-1-ol

: 948995-21-9
(2R,4S,5R)-5-[3-(tert-butyldimethylsilyloxy)propyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / CBr₄; PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

2: 96 percent / acetonitrile / 27 h / Heating

3: 75 percent / LiHMDS; HMPA / tetrahydrofuran; hexane / -78 - 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; carbon tetrabromide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 3: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0708442