(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

Base Information

Chemical Name:(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal
CAS No.:444682-17-1
Molecular Formula:C₂₄H₃₆O₅
Molecular Weight:404.547
Hs Code.:

Synonyms:(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

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Chemical Property of (Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

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Technology Process of (Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

There total 12 articles about (Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-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: 91.0%

: 623926-34-1
(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol

: 444682-17-1
(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

Guidance literature:: With Dess-Martin periodane;
DOI:10.1021/ol026084t

Reference yield:

: 106296-58-6
(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol

: 444682-17-1
(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

2.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

2.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

3.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

4.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.2: Wittig reaction / 5.1: Dess-Martin oxidation;
DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

: 184291-95-0
(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

: 444682-17-1
(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

1.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

2.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

3.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; Dess-Martin periodane; ozone; In tetrahydrofuran; methanol; dichloromethane; 2.2: Wittig reaction / 4.1: Dess-Martin oxidation;
DOI:10.1016/S0968-0896(03)00186-X