(4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane

Base Information

Chemical Name:(4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane
CAS No.:1044518-74-2
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane

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Technology Process of (4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane

There total 12 articles about (4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-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: 88.0%

: 100-39-0
benzyl bromide

: 2-[(4S,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol

: 1044518-74-2
(4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane

Guidance literature:: With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; 0 deg C -> rt;
DOI:10.1021/jo00189a046

Reference yield:

: 100-39-0
benzyl bromide

: 1044518-74-2
(4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 24h; Inert atmosphere;
DOI:10.1002/anie.200800589

Reference yield:

: 90941-89-2
(E)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

: 1044518-74-2
(4R,6S)-6-(2-(benzyloxy)ethyl)-4-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 8 steps

1: 77 percent / Ti(O-i-Pr)4, diethyl (-)-tartrate, TBHP / CH₂Cl₂ / -20 °C

2: 76 percent / Redal / tetrahydrofuran / -20 °C

3: 65 percent / NaH / hexamethylphosphoric acid triamide; dimethylformamide / Ambient temperature

4: 100 percent / 0.8percent H₂SO₄ / methanol / Ambient temperature

5: 85 percent / imidazole / tetrahydrofuran / Ambient temperature

6: 98 percent / CSA catalyst / acetone / Ambient temperature

7: 98 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

8: 88 percent / NaH, 18-crown-6 / tetrahydrofuran / 0 deg C -> rt

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2S,3S)-tartrate; sulfuric acid; sodium; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; CSA catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ammonia; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00189a046