(2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal

Base Information

• Chemical Name: (2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal
• CAS No.: 595559-34-5
• Molecular Formula: C₁₈H₂₉NO₄
• Molecular Weight: 323.433

Synonyms:(2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal

Chemical Property of (2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal

There total 13 articles about (2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal 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: 74.8%

(2RS,4S)-4-(benzyloxy)-2-[(E)-but-2-enyl]-5,5-dimethoxypentanal oxime (595559-32-3) → (2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal (595559-34-5)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; acetic acid; at 0 ℃; for 1.16667h;

DOI:10.1002/hlca.200390125

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal (595559-34-5)

Guidance literature:

Multi-step reaction with 11 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

11.1: 74.8 percent / NaBH₃CN / acetic acid; tetrahydrofuran / 1.17 h / 0 °C

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

DOI:10.1002/hlca.200390125

Reference yield:

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (2S,2RS,6E)-2-(benzyloxy)-4-[(hydroxyamino)methyl]oct-6-enal dimethyl acetal (595559-34-5)

Guidance literature:

Multi-step reaction with 12 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

12.1: 74.8 percent / NaBH₃CN / acetic acid; tetrahydrofuran / 1.17 h / 0 °C

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

DOI:10.1002/hlca.200390125

upstream raw materials:

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

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

L-glutamic acid

Downstream raw materials:

(4R,5S,7R,9S)-9-(benzyloxy)-4-methyl-3-oxa-1-azatricyclo[5.3.1.0^5,10]undecan-2-one

(4S,5R,7S,9S)-9-(benzyloxy)-4-methyl-3-oxa-1-azatricyclo[5.3.1.0^5,10]undecan-2-one

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