(2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime

Base Information

Chemical Name:(2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime
CAS No.:595559-32-3
Molecular Formula:C₁₈H₂₇NO₄
Molecular Weight:321.417
Hs Code.:

Synonyms:(2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime

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Chemical Property of (2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime

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Technology Process of (2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime

There total 12 articles about (2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime 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:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 595559-32-3
(2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime

Guidance literature:: Multi-step reaction with 10 steps

1.1: 77.7 percent / Et₃N / CH₂Cl₂ / 20 h / 22 °C

2.1: NaH; [15]crown-5; H₂O / benzene / 6 h / Heating

2.2: benzene / 17 °C / Heating

3.1: 22.73 g / DIAD; PPh₃ / tetrahydrofuran / 3 h / 23 °C

4.1: 11.72 g / ZnBr₂ / methanol; CH₂Cl₂ / 3 h / 23 °C

5.1: 11.72 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 5.885 g / TsOH*H₂O / methanol / 1 h / 23 °C

7.1: BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 5.5 h / 65 °C

8.1: 7.982 g / LiAlH₄ / tetrahydrofuran / 16 h / 22 °C

9.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 22 °C

10.1: 7.926 g / NH₂OH*HCl / ethanol; pyridine / 1 h / 23 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 15-crown-5; di-isopropyl azodicarboxylate; hydroxylamine hydrochloride; water; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc dibromide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; benzene; 5.1: Swern's protocol / 7.1: Ireland-Claisen rearrangement;
DOI:10.1002/hlca.200390125

Reference yield:

: 595559-29-8
(E)-2-((S)-2-Benzyloxy-3,3-dimethoxy-propyl)-hex-4-enal

: 595559-32-3
(2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime

Guidance literature:: With hydroxylamine hydrochloride; In pyridine; ethanol; at 23 ℃; for 1h;
DOI:10.1002/hlca.200390125

Reference yield:

: 21461-84-7
(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

: 595559-32-3
(2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime

Guidance literature:: Multi-step reaction with 11 steps

1.1: 85.1 percent / BH₃*SMe₂ / tetrahydrofuran / 3 h / 20 °C

2.1: 77.7 percent / Et₃N / CH₂Cl₂ / 20 h / 22 °C

3.1: NaH; [15]crown-5; H₂O / benzene / 6 h / Heating

3.2: benzene / 17 °C / Heating

4.1: 22.73 g / DIAD; PPh₃ / tetrahydrofuran / 3 h / 23 °C

5.1: 11.72 g / ZnBr₂ / methanol; CH₂Cl₂ / 3 h / 23 °C

6.1: 11.72 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

7.1: 5.885 g / TsOH*H₂O / methanol / 1 h / 23 °C

8.1: BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 5.5 h / 65 °C

9.1: 7.982 g / LiAlH₄ / tetrahydrofuran / 16 h / 22 °C

10.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 22 °C

11.1: 7.926 g / NH₂OH*HCl / ethanol; pyridine / 1 h / 23 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 15-crown-5; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; hydroxylamine hydrochloride; water; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc dibromide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; benzene; 6.1: Swern's protocol / 8.1: Ireland-Claisen rearrangement;
DOI:10.1002/hlca.200390125