(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

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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-en-1-ol
CAS No.:856410-58-7
Molecular Formula:C₂₆H₄₂O₅Si
Molecular Weight:462.702
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-en-1-ol

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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-en-1-ol

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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-en-1-ol

There total 10 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-en-1-ol 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:

: (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

: 856410-58-7
(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

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; hydrogenchloride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
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

: 856410-58-7
(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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 848691-93-0
dimethyl 2-{(4R,5S)-2,2-dimethyl-5-[2-(4-methoxybenzyloxy)ethyl]-[1,3]dioxolan-4-yl}-2-oxo-ethyl-1-phosphonate

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 70 percent / K₂CO₃ / tetrahydrofuran; H₂O / 20 °C

2.1: 80 percent / NaBH₄; CeCl₃*7H₂O / methanol / -78 - 20 °C

3.1: DEAD; PPh₃ / benzene / 20 °C

3.2: TBAF / tetrahydrofuran / 20 °C

3.3: neocuproine / Pd₂(dba)3 / toluene / 20 °C

4.1: 89 percent / HCl / methanol / 20 °C

5.1: 87 percent / DDQ / CH₂Cl₂ / 0 °C

6.1: 90 percent / imidazole / dimethylformamide / 20 °C

7.1: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: Horner-Wadsworth-Emmons reaction / 3.1: Mitsunobu reaction;
DOI:10.1002/anie.200500029