(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

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Chemical Name:(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal
CAS No.:856410-59-8
Molecular Formula:C₂₆H₄₀O₅Si
Molecular Weight:460.686
Hs Code.:

Synonyms:(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

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Chemical Property of (E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

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Technology Process of (E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

There total 12 articles about (E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal 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: 96.0%

: 856410-58-7
(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-en-1-ol

: 856410-59-8
(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

Guidance literature:: With Dess-Martin periodane;
DOI:10.1002/anie.200500029

Reference yield:

: (2E,5Z)-(S)-1-{(4S,5S)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hepta-2,5-diene-1,7-diol

: 856410-59-8
(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / PdCl₂(CH₃CN)2 / tetrahydrofuran / 3 h / 0 °C

2: 89 percent / HCl / methanol / 20 °C

3: 87 percent / DDQ / CH₂Cl₂ / 0 °C

4: 90 percent / imidazole / dimethylformamide / 20 °C

5: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 96 percent / Dess-Martin periodinane

With 1H-imidazole; hydrogenchloride; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 6: Dess-Martin oxidation;
DOI:10.1002/anie.200500029

Reference yield:

: Carbonic acid (2E,5Z)-(S)-7-hydroxy-1-{(4R,5S)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hepta-2,5-dienyl ester methyl ester

: 856410-59-8
(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

Guidance literature:: Multi-step reaction with 6 steps

1: 59 percent / neocuproine / Pd₂(dba)3 / toluene / 80 °C

2: 89 percent / HCl / methanol / 20 °C

3: 87 percent / DDQ / CH₂Cl₂ / 0 °C

4: 90 percent / imidazole / dimethylformamide / 20 °C

5: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 96 percent / Dess-Martin periodinane

With 1H-imidazole; hydrogenchloride; 2.9-dimethyl-1,10-phenanthroline; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Dess-Martin oxidation;
DOI:10.1002/anie.200500029