(2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

Base Information

Chemical Name:(2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal
CAS No.:565229-36-9
Molecular Formula:C₂₈H₄₄O₇
Molecular Weight:492.653
Hs Code.:

Synonyms:(2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

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Chemical Property of (2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

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Technology Process of (2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

There total 16 articles about (2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-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: 81.0%

: (Z)-(2S,3S,4S)-3-(4-Methoxy-benzyloxy)-8-((2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-oct-5-en-1-ol

: 565229-36-9
(2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

Guidance literature:: With Dess-Martin periodane; In dichloromethane;

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 565229-36-9
(2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

Guidance literature:: Multi-step reaction with 7 steps

1.1: 64 percent / pyridinium p-toluenesulfonate / benzene / 3 h / Heating

2.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: I₂; imidazole; triphenylphosphine / CH₂Cl₂ / 1 h / 0 °C

4.1: 4.5 g / benzene / 36 h / Heating

5.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

5.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

6.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

7.1: 270 mg / pyridinium sulfur trioxide; N,N-diisopropylethylamine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; benzene; 5.2: Wittig olefination;
DOI:10.1021/jm0204136

Reference yield:

: 479673-37-5
(2S)-2-[(4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propan-1-ol

: 565229-36-9
(2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

Guidance literature:: Multi-step reaction with 5 steps

1.1: I₂; imidazole; triphenylphosphine / CH₂Cl₂ / 1 h / 0 °C

2.1: 4.5 g / benzene / 36 h / Heating

3.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

3.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

4.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

5.1: 270 mg / pyridinium sulfur trioxide; N,N-diisopropylethylamine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; iodine; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; benzene; 3.2: Wittig olefination;
DOI:10.1021/jm0204136