(2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Base Information

Chemical Name:(2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane
CAS No.:883292-60-2
Molecular Formula:C₃₀H₅₆O₅Si₂
Molecular Weight:552.943
Hs Code.:

Synonyms:(2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

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Chemical Property of (2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

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Technology Process of (2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

There total 10 articles about (2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[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: 85.0%

: 883292-58-8
(2S,3S,4S,5S,6S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-heptane-1,3-diol

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 883292-60-2
(2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tetlet.2006.01.105

Reference yield:

: 936637-19-3
(2R,3S,4S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide

: 883292-60-2
(2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 6 steps

1: DIBAL-H / tetrahydrofuran / -78 °C

2: NaH / tetrahydrofuran / -78 °C

3: DIBAL-H / CH₂Cl₂ / -78 °C

4: m-CPBA / CH₂Cl₂ / 0 °C

5: 87 percent / tetrahydrofuran / -78 - -20 °C

6: 85 percent / PPTS / CH₂Cl₂ / 20 °C

With pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 2: Horner-Waddsworth-Emmons homologation;
DOI:10.1016/j.tetlet.2006.01.105

Reference yield:

: (E)-(4S,5R,6S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

: 883292-60-2
(2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 3 steps

1: m-CPBA / CH₂Cl₂ / 0 °C

2: 87 percent / tetrahydrofuran / -78 - -20 °C

3: 85 percent / PPTS / CH₂Cl₂ / 20 °C

With pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2006.01.105